Country Music in the 90’s: The Year is 1999

Hey, welcome to the final episode of the 90s Country Podcast. This episode is all about capping off a decade that took the country music.

Genre to a whole new level.

I'll be counting down the top 10 country music moments of 1999 on this episode. So without spoiling anything, let's jump right into it.

Number 10.

The Grand Ole Opry House turned 25 years old. When people talked about country music in 1999, the conversation was usually around sales and numbers. who crossed over, who sold millions, who filled arenas. But that same year, the Grand Ole Opry House quietly turned 25 years old. And that anniversary mattered just as much, if not more than any number. Because, by 1999, the sound of country stretched far beyond what it was in 1974 when the Opry House first opened its doors. Production had become much bigger. Crossover and country music wasn't just an experiment anymore, it was normal. Artists were debuting on pop charts, country tours were running like major label pop productions. The business had taken itself to

a whole new level. And through all the expansion, though, the Opry remained steady. It didn't pivot when trends shifted. It didn't try to chase whatever radio was leaning toward that month. It stayed rooted in what it had always represented. Live performance, songwriting, tradition, credibility. By 1999, that building had watched the urban cowboy wave, the neo-traditionalist reset, the superstar boom of the 90s, all come and go through its doors at the Opry House. So the 25-year mark wasn't just an anniversary, it was a reminder. It reminded people that while country music was evolving commercially, there was still an institutional backbone holding the identity together. And that balance was important at the end of the decade, because without

something stable like the Opry, rapid growth can blur what a genre is and what a genre represents. The Opry's presence in 1999 reinforced the that even as the format chased new audiences, it still valued its roots. The stage still meant something different than a tour stop. It carried history. There wasn't a number one single attached to the anniversary.

There wasn't a headline-grabbing controversy, but culturally, it mattered. It symbolized continuity at a moment when country music was expanding faster than it ever had. And heading into the 2000s, that balance between growth and grounding was going to matter more than people realized at the time.

Number nine.

Keith Urban makes his solo debut. By the end of the 90s, Keith Urban was still new to most American country music fans. But in 1999, Keith made a solo introduction with the release of his self-titled American debut album called Keith Urban. And for those that don't know, and most of you probably do, Keith was in a band called The Ranch. But now we're talking about Keith Urban, the solo artist, and the album Keith Urban. That album introduced a sound that would carry his career into country superstardom just like he's in today. The guitar was front and center, not just a shiny toy, not just a prop, but as the foundation. His overall feel was modern with the music, and it was different from what most country

radio was playing at the time. The album's first single, It's a Love Thing, did not explode, but it got him on the board, reaching the top 20 and introducing him to U.S. country radio. The next song was called You're Everything. It got to number four, so a little more. And suddenly Keith Urban wasn't just a new name, but one that people were starting to take seriously. And it was the first real sign that his album, Keith Urban, was going to have some legs to it. But the real breakthrough came with But For The.

Grace Of God.

That was the third song, the third release. This song went all the way to number one, giving Keith Urban his first number one song in the U.S. and changing the trajectory of his career for decades to come. But that album didn't stop there. Where The Blacktop Ends, such a great song. it reached the top five. It was not a number one, which is crazy because I still know it and sing it now. But every major single from that album landed inside the top 20 and he did have a number one. So when you step back and look at it, this album wasn't instant dominance for Keith. Heck, it only had one number one, but it did create momentum.

Each release built on the last. Introduction, recognition, validation. Keith got that number one. He was not a question mark anymore. So The album didn't just introduce him, it established him and his style in the country music scene. And when you look at everything that followed, the hits, the longevity, the role he'd eventually play in shaping modern country music, for him, as a solo artist, it all started in 1999 with the release of his first solo album. And I was talking to Keith about his origin story, about when he first moved to Nashville from Australia to just get some perspective on how far he had come.

Weirdly enough, the first place that I stayed with my manager when we came here, the very first trip, we stayed over the road at Shoney's Inn, which is now Comfort Inn. And the room that we stayed in is literally right there. And it's crazy to walk out the door of the studio and look over and see that room.

that my manager and I stayed in on the first trip. And to go from there to here is mind boggling.

So why do you say you and your manager, you guys came together here?

What was that relationship?

We, you know, we just, I made a little demo tape that we just got on a plane and came over here. We really didn't know anybody. We just did the classic thing of walking up and down 16th and 17th Ave and going in and seeing if they'd let us play them my little cassette demo.

So you record a cassette of songs. How many songs do you think?

Just guessing.

Maybe five or six songs that I'd written.

And you felt strongly enough about it that we're going to go to Nashville.

He felt strongly enough about you. Yeah. That's a lot of trust under a person too, by the way. Like as a manager going, I trust this guy. Like this is my guy. You fly here. You're staying at the Shoney's Inn. Yeah. For what do you think a night?

How much?

Oh, more than we could afford at the time. I mean, we spent everything we had on the plane ticket, you know.

Paying nightly rent.

Yeah. And then.

How do you do it?

Again, you're knocking on doors, but what doors do you knock on if you don't know what doors are important?

Anybody that would listen, we would play it for. And I was so proud of it, you know, and thought, oh, I can't wait for everybody to hear this.

It was terrible.

In hindsight, it was just terrible. What do I know?

But played it for people that would listen to it, and it was all very much like, thanks, but, you know. And so it was really heartbreaking, you know. It was just soul-sucking. But I went, anyway, I want to be here. I want to live here.

Let's go.

Let's go. When you say let's go, do you go back? Yeah, so I was.

Only on a– it was really hard to get visas back then. And I couldn't legally stay longer than, you know, a certain period of time. I couldn't make any money here, not legally. So I could come for a couple of weeks, try and get with people to write, and then I'd have to go back to Australia. And I was doing– little shows at corner pubs or wherever I could on my own solo to just stock money away. So I could then get another plane ticket, come back and just keep doing this back and forward forever.

How long did you go back and forth?

I don't know, two, three years, something like that. I would come over for a couple of weeks and write with some people and then go back and come back over. But I was staying in a hotel, probably down here at the Shoney's, I think still. And This guy who was an engineer at one of the publishing places I went to, he said, listen, I live on my own.

I've got a spare room at my house if you want to stay there instead of a hotel. So I stayed at his house. And when I left to go back to Australia, I left a bunch of clothes in the drawer. And he called me and he goes, hey, you left some stuff here. And I said, yeah, I'll be back because I wanted to feel like I was moving in. So I was in Australia thinking, I've got clothes in Nashville like I have It was like saying I have a place there.

Or you left a toothbrush at somebody you're dating's house, so now you know.

Same kind of thing. Yeah, you got to go back.

Exactly.

Number eight.

George Strait kept showing up at number one. By the time the song Write This Down came along, a George Strait song going number one, it almost felt inevitable, which is exactly why it stands out in a 1999 countdown. By the end of the decade, country radio didn't really have one clear sound because records were getting bigger. Styles were spreading out. Artists were taking very different approaches to try and stay relevant. But not George Strait. He stayed right where he was. Write This Down sounded exactly like you would think a George Strait song would sound. Straightforward, clean, centered on the song itself. He did not need a reinvention.

There was no adjustment. And this song still went number one. That's the part worth talking about on this countdown, because in a year... filled with different styles, heck, in a decade with different styles, everybody competing for attention, the very familiar George Strait approach continued to connect at the highest level.

It showed just how steady his presence had become with fans and inside of country music altogether.

And at this point, this wasn't a comeback. It wasn't a surprise hit.

It was just another chapter in a very long, a very consistent long run for George Strait. And when you talk about those runs in the 90s, nobody did that better than George. because Write This Down spent multiple weeks at number one. It closed out the decade as the 17th and final number one of the 90s, which was the most of any artist in the 90s. And that's not easy to pull off, especially as the sound of the format kept shifting throughout the decade. Most artists eventually adjust.

They change lanes. They update their sound. They react to where things are going. George Strait didn't do that. And Write This Down is a good example of why. So this isn't about one song being bigger and changing and number one for the first time. It's about consistency. And it's about continuing to hold its place even as everything else around changed. And that's why this moment belongs on the countdown for 1999.

A 1999 bonus The new Y2K panic.

Back in 1999, one of the biggest things hanging over everybody's head, especially in pop culture, but.

Really in life. It wasn't a movie.

It wasn't a song. It wasn't a celebrity breakup. It was the Y2K panic. And the concern was simple. A lot of computer systems had only been programmed to recognize the last two digits of a year. So instead of reading 2000, they would just read 00. And if that happened, computers would think we're back to 1900. So we wondered, would everything crash? That idea alone of zero-zero opened the door to a lot of uneasy questions. Banks, air traffic systems, power grids, anything that relied on dates suddenly felt vulnerable.

The fear wasn't about one thing breaking. It was about a lot of things breaking at the same time. The image that stuck with people was the modern world glitching out right when midnight hit and it was over. And because this also lined up with the end of the millennium, everything about it felt bigger. News coverage ramped up. Experts debated worst-case scenarios. Survival kits flew off shelves. People pulled cash from banks. People stocked up on food and water just in case. Even if you didn't fully buy into the panic, it was hard to ignore just how loud and constant the conversation was. And that's what turned Y2K into more than a technical issue. It was a cultural moment.

Less about code, but more about uncertainty. The feeling that the future was arriving all at once and nobody knew exactly what would happen once it did. And then Midnight arrived. The clock switched over. January 1st, 2000 showed up and for most people, nothing happened. No widespread failures, no shutdowns, no collapse, which almost made the whole thing even more fascinating.

After all the buildup, all the anxiety, all the nonstop coverage, Y2K ended up standing as one of the clearest examples of how fear and anticipation can completely take over the moment, even when the outcome turns out to be quiet. And that's why people still remember it.

Hang tight. The Bobbycast will be right back.

Number seven.

Toby Keith reaches a new level with How Do You Like Me Now? By the time Toby Keith released his song, How Do You Like Me Now, in November of 1999, he already had a solid resume. But no song that he'd released before, How Do You Like Me Now, had results like this one. On country radio, the performance was immediate and it was lasting. That song reached number one on Billboard's Hot Country Songs chart and stayed there for five weeks in early 2000. That alone put it among the longest-running number ones of his career to that point.

More importantly, it did not just peak.

It lingered.

By the end of the next year, Billboard had named it the number one country song of 2000. That is some serious lingering. Heck, none of Toby Keith's songs had ever finished a year at the top of the overall country rankings. Much less The year after it had come out. And the crossover numbers reinforced how far the song reached beyond just country radio. How Do You Like Me Now climbed to number 31 on the Billboard Hot 100, which is all songs, even pop songs. And that's the highest he'd ever been. Should've Been a Cowboy, Who's That Man, Me Too. Massive country records, but they did not get that pop level, that chart visibility. Not only did the song go platinum, but the album went platinum as well.

And it was titled How Do You Like Me Now. And the thing is, the album did not jump off shelves at the beginning. The original lead single was When Love Fades. You would say it underperformed. And it looked like the album might stall. But once that title track was released, the entire trajectory completely flipped because radio play surged.

Sales followed.

The album's commercial life was effectively restarted, which didn't happen a lot then. And then we could talk about awards because Recognition tracked closely with the numbers. The song got nominations for ACM Single of the Year and Song of the Year, and the album won Album of the Year in 2001. The nominations and the win showed that it wasn't just good with Toby Keith good, it was one of the defining commercial releases in country music in 1999 and the years that followed. And when you strip the story down to results, the difference is clear. Toby Keith had number ones before. He had recognizable songs before. He had steady sales before. But what he didn't have before 1999 was a single that led the entire format for

a full year. That crossed over into pop charts. That got him to a career high level. That sold a million copies and pulled an album to platinum. The combination is rare even for established artists. And that's why his single, How Do You Like Me Now, stands apart. Not because of what it represented, because that was awesome too, but because of what it produced. on charts, at retail, and across an entire release cycle. To put in perspective just how big and successful Toby got during his 90s run and beyond, I wanted to play this when he.

Was back in studio with me a few years ago.

I was talking to Toby about potentially running for office one day. He shot that down before dropping a line about making some money and making more than the president does, something we all still laugh about and joke about in our studio today.

It'd be really hard to run that show because everybody around you would either be a yes man or a liar.

You don't feel like you can break that mold, though?

No.

Don't you feel like you broke a mold in country music and you don't feel like you can break a mold in politics?

No, I could put a niche in, maybe at the city level or something, but plus the pay sucks.

That's about power, though.

That's not even about pay.

I can make more than a night and the president makes all year.

In a night, you can make over $ 100, 000?

You brought it up, not me.

He makes more than $ 100, 000.

I'm just asking, though. In a night, you can make over $ 100, 000?

Oh, yeah.

Oh, my goodness.

Holy crap.

You're simple.

I am simple.

What's a president make a year?

Like $ 250, 000?

Is that what the salary is for the president?

I think it's about that.

Is it $ 250, 000, right?

In a night, you can make over $ 250, 000? I've made that much in merch before.

In a night?

In a night.

Can I touch you?

Number six, number six, number six.

Brad Paisley's arrival made an immediate statement. Before country music fans had ever heard the name, Brad Paisley had already been putting in the work as an artist. He was known first as a strong guitar player, a student of traditional country, someone who understood the history of the genre long before he ever put out a single. He spent time writing and touring and learning how the format worked from the inside. But None of that really matters until the first song hits. And when Brad Paisley finally arrived on country radio, he did not ease into it. His second ever single was called He Didn't Have To Be.

It showed up near the end of 1999. It stood out immediately. The song was co-written by Brad and Kelly Loveless, and it's based on a real-life story of Loveless' relationship with a stepson. The writing was specific, the story was clear, and the delivery didn't feel like he was trying to match what anyone else was doing at the time. And at the time, country radio was full of those big voices we've talked about it was full of polished production that we've talked about a lot of songs sounded good but not all of them pulled you into the story like he didn't have to be dead it told a complete narrative from start to finish and in just one song it gave listeners a clear sense of who brad paisley was not just as a singer but as a

songwriter someone who valued detail someone who trusted storytelling more than flash that's a strong place to start your career And the response to the song said it all. He didn't have to be climbed all the way to number one in December of 1999. Brad did not need a few more singles to find his footing in country music.

From the start, the writing, the tone, the approach, everything was lined up. When you look at everything that followed, the guitar work, the humor, the storytelling, it all traces back to this first impression. Or second, since it was his second single. So it's not just about a debut. It's about how clear and immediate his early music was.

It introduced Brad Paisley, fully formed, he connected immediately, and he set the foundation for a long run without ever needing to adjust a picture. As I said a little bit ago, Brad is known for his awesome ability to play guitar. One time, I saw a picture of his guitar in a freezer on social media, so I asked him what that was about.

It's a really long story. It's one of those anal strange things. Well, anal might be the wrong word, but it's one of those really strange things. Like things where I get obsessive about going and making guitars exactly what they ought to be. And over time, the finish cracks. And they sound better because the finish loosens up from the body. So if you take a new guitar and you put it in the freezer, the finish cracks and all these little hairline cracks, and I swear it sounds better.

I can tell.

Number five.

Kenny Chesney's career-altering song release. When you looked at Kenny in 1999, the shift wasn't just in his songs. It was how his fans were starting to understand him. Because before that point, he'd been around. He'd released records. He'd had some radio success. Nashville knew the name. And there were enough signs that something could work. But it didn't always feel defined. He wasn't the Kenny Chesney selling out stadiums quite yet. And that's a common stage for artists early in their career.

The songs can be good. The voice can be there.

But the identity, the thing that makes someone instantly recognizable, isn't locked in yet. By 1999, that started to change. And his song, You Had Me From Hello, went number one. That song did what you would expect a number one to do on country radio because it fit clean, it connected. It's a good song. No controversy, no debate. Just a win all the way around. And then he followed it up with She Thinks My Tractor Sexy. That song was not easy. It's kind of funny. That release immediately shifted how people talked about Kenny Chesney. The title alone grabbed attention, and once you played it, you could hear that the song was funny, and it was an exaggeration. And at the time, country records did not have much humor or exaggeration.

It was looser and louder and playful, and listeners loved it.

And some didn't. Some rolled their eyes. But everybody had an opinion.

And I was talking with Kenny Chesney, and he hadn't played that song, She Thinks My Tractor Sexy, for a long time. But another artist convinced him to put this song back in a set list.

We do Tractor every now and then.

There's a moment that I got really sick of Tractor. Like, I just thought, well, if I don't have to sing Tractor anymore, it's not going to hurt my feelings. But then Megan Maroney comes out on the road with us.

She's out there for a couple weekends and she goes, why are you not doing Tractor? I want to hear Tractor. She goes, everybody out there wants to hear Tractor. I want to hear Tractor. And I said, OK, well, you're going to come up and sing it with me. And she goes, deal. And then I did it and she was right.

They go crazy.

It's just, it's like, okay, me mentally, I'm past it, but it's, it will forever be there, you know? And that's when she and I became, started to become really good friends, you know? So, but that's how I started. That's how I started playing tractor again. It was because Megan more or less forced it on me.

What's interesting.

When you look back at that chart performance, that song never reached number one. It did not even crack the top 10 yet. Everybody knows all the words. culturally massive. And that's what makes this song a defining moment. The chart position didn't tell the whole story. That song lived far beyond its radio run. It became one of those records that people remembered instantly and one that is tied directly to Kenny Chesney. Up until that point, he had momentum, but his image wasn't fully set. This song changed all of that. It revealed he had a sense of humor.

It revealed he had comfort with being a little over the top. And it revealed that he was willing to stand out in a crowded format. In the late 90s, there was no shortage of talent on country radio, and being able to identify an artist right away by a single song or sound, that was hard. But Kenny did that, and that song helped. So when you step back and you look at this stretch of his career, the numbers only tell part of it. Yeah, You Had Me From Hello was the number one song. But She Thinks My Tractor's Sexy is a song that really stuck out then and still sticks out today.

It didn't top the chart. It didn't need to.

From that point forward, people just didn't recognize Kenny's name. They understood who he was. And that's why this moment belongs here. Jodi Messina's record-setting run of number ones. Jodi Messina entered 1999 with a lot of momentum after her song Bye Bye broke through in 1998. Now what followed that breakthrough was a late 90s chart run that hadn't been seen before from any female country artist. I was talking to Jodi Messina about that period in her career.

I asked if there was a moment in the late 90s where she felt invincible as an artist.

I remember Byron Gallimore telling me, my producer saying, I was like, oh man, it would be so great to have a number one record. And he goes, yeah, but then you got to have another one. And so you were so in the chase for.

The next one for me. And then again, you're insecure, right?

So you were like, oh gosh, I got to have another one or else I'm done or else whatever. I remember Downtime came out. And it peaked at number eight. What I would do for a number eight song right now, not really, I mean, but it would be such a thrill to have a number eight song, right?

I'd be like, oh my gosh.

But as soon as that song maxed out at number eight, they're like, well, she's done.

She's done. She's over.

At that point, you know, everyone was so disappointed. And I felt like they were disappointed in me. I was like, I am a failure. So I don't know that there ever was a point where I felt bulletproof. No, it was always about working harder.

If you could do it again or you could tell you back then, like right when it was starting to hit, like right before you got your first number one, you have a deal.

What advice would you give yourself then? I always say this.

Don't sell out who you are. Just be successful.

Do you feel like you did that?

I think there were moments, yes, where I did that. And I would look at pictures and be like, oh, boy, I remember that.

You know, there was a point where I was myself, then we had some success, and then all of a sudden the people would flock and be like, wear this, do that. We had a photo shoot, and I remember looking at these photos. My hair was bone straight, long, down to here, all these, like, couture clothes.

And I was like, I don't know who that is. And they're like, oh, but you look beautiful. I'm like, yeah, but... I don't know who she is. Like, I don't know who that is.

Who is that?

I can't, I said, I don't go to Kroger looking like this.

You know, people, they would never see me look like that.

You know, I can't sell that. Why would I represent something that I'm not?

Ooh, which that was a, then, then back then it was like, oh, we were being difficult.

Oh, she's hard to work with. And it was really just, I can't pretend.

I can't pretend to be something that I'm not.

It's crazy and refreshing to hear her talk so openly about those early insecurities, but that hunger and, And that doubt is also what fueled the historic run that you're about to hear about. Bye Bye reached number one and stayed there for two weeks. She followed Bye Bye with I'm Alright, which also went to number one and held the top spot for, again, more than a week. Two consecutive number one singles from the same album from a female artist. Then there's the third release, Stand Beside Me, which also reached number one in January of 1999 and stayed there for three weeks. And with that song, Jodi Messina became the first female country artist to have three Multi-week number one singles from a single album. That's why

we're here in 1999 talking about it. Together, Bye Bye, I'm Alright, and Stand Beside Me kept her at number one for eight total weeks with one single rolling directly into the next. It was pretty much impossible to turn on country radio in 1999 and not hear a Jodi Messina song playing. Then her next single, Lesson in Leavin', peaked at number two and remained there for seven weeks, ending the streak. But a seven-week number two, that is crazy.

You know you're doing something right as an artist when a song hits number two on the charts and a number two ends your historic streak.

And that's what she was doing. She was killing it.

And by the time she won the CMA Horizon Award later that year, which was Best New Artist, the chart run was already complete. Three multi-week number one singles, eight total weeks at the top, all from one album. When you look back on it now, Jodi's 1999 just never really let up. That's what makes it stand out, and that's why we put it on the countdown. A defining moment of 1999 was Woodstock 99. You really can't talk about music in 1999 in general without bringing up Woodstock 99.

It took place July 22nd through the 25th at an old Air Force base in Rome, New York. It was massive, anywhere from a couple hundred thousand people to almost 400,000, depending on who you ask. And the idea was to recreate Woodstock for.

A new generation. And on paper.

The lineup made sense. It was the biggest bands at the time. Metallica, the Chili Peppers, Limp Bizkit, Korn, Rage Against the Machine, Dave Matthews Band. It was a snapshot of late 90s music. MTV was there covering the event. Pay-Per-View brought it all to everybody's living room. And for a minute, it felt like the biggest thing happening in music that summer. But once people got there, the reality set in fast. And if you've ever seen the documentary, you know what I'm talking about. The site was mostly concrete.

It was at an Air Force base. There wasn't much shade. It was extremely hot.

I mean, it was July.

And the basic stuff like water, food, and bathrooms quickly became issues. As the weekend went on, frustration, because there was no water, food, and bathrooms, the frustration just kept building. By the time the final night rolled around, things completely fell apart. What people remember now isn't the performances. It's the fires and the rioting. and the damage across the grounds. Afterwards, there were reports of assaults, injuries, three deaths. The images that stuck weren't of the bands on stage, but the fires burning all around them. From that point on, Woodstock 99 stopped being remembered as a festival and started being referenced as a lesson. It still comes up whenever big events are talked about. Crowd control, safety, planning, heck, water.

All of this as an example of what happens when when scale gets ahead of infrastructure. A lot of the changes you see at festivals now trace back to what went wrong there. Plenty of things from 1999 feel like time capsules, but Woodstock.

99 still gets picked apart.

Not just because it went wrong, but because of how big the wrong was, how public the wrong was, and how fast it unraveled.

Number three.

Tim McGraw released his fifth studio album, A Place in the Sun, in May 1999. The album debuted at number one on both the Billboard 200 and the Top Country Albums chart, which was a first for Tim to just be on the Billboard 200. That debut made it clear right out of the gate where this album was heading.

A Place in the Sun went on to sell more than 4 million copies in the United States and was four times platinum. What made it so impressive was the album didn't have one big moment or one big song. It just kept building as each song came out. And even 30 years after the release of this album, Tim is as relevant as ever.

Why?

Because of his consistency. And fun fact, Tim McGraw is the most played artist in country radio since the nineties. So I was talking to Tim and how does he keep doing it over and over and over year after year, decade after decade.

So I asked him, I just feel fortunate. You know, I get, you know, great songwriters send me great songs. I get to work with Byron Gallimore in the studio. Who's one of the best in the world. And we've worked together since the beginning of my career. I feel very fortunate. I feel very fortunate to have the opportunity to, to record great songs, and to still get the chance for people to hear them.

And if we're talking about A Place in the Sun, you see what I'm talking about here. The producer he referenced there, Byron Gallimore, produced this album way back in the day alongside Tim and James Stroud. The album produced five major singles. Four of those reached number one. It all started when he released Please Remember Me, which reached number one. Then it was followed by Something Like That, which hit number one in the summer of 99. Then My Best Friend was released, and that was number one as well. The fourth number one single, My Next 30 Years, carried the album's chart activity into the following year, keeping A Place in the Sun as relevant as ever. The only single that did not reach number one, and by

the way, we're four number ones in, was Some Things Never Change. That peaked at number seven. As a result, every major single released from that album landed inside the top 10. Again, you got four number ones and a number seven.

Not bad.

And if we talk about awards, at the 1999 CMAs, A Place in the Sun won Album of the Year, and Tim McGraw was named Male Vocalist of the Year. This was Tim's second Album of the Year award, but it was his first time winning Male Vocalist of the Year.

And when you look.

At Tim McGraw's run in 1999, A Place in the Sun stands as a complete commercial cycle. Number one debut, multiple number one singles, consistent top ten placement across all releases, and long-term sales that extended well beyond the release window.

Like it just kept selling.

And when you think about where Tim was at the beginning of the 90s compared to where he was when it ended, it's a massive leap. A Place in the Sun sits right in the middle of that. It meant so much to Tim's growth. And what's funny about Tim is that he's just like anyone else in the creative space when he listens to his old stuff. He cringes, even after decades of success. And I asked him if he ever listens back to his old songs.

I don't go back and listen very often.

The only time that I listen to to something is, is when I'm getting ready to do, to do a new project, I'll go back and listen to the last record that I made because, you know, you, you never really finish a project. You just sort of get it in the barrel, so to speak. So I always make mental notes of things that I wanted to do better, things I wanted to improve, sounds that I wanted to improve, certainly singing that I wanted to improve.

So I'll go back and listen.

I go, I remember I wanted to do something different here and I didn't get the chance to do it. So I'll remember that the next time I go to the studio to record.

Do you, when you say you listen to something and you're like, Ooh, cause I'll, we all do that, right? If I look at old, or listen to old.

Shows or old, I'm always like, Oh man, I don't like how I did that there. But when you hear you and you say you cringe, is it because you don't feel like you sang as well? Or was it because maybe it was produced weird?

No, not produced.

We're probably more, more of my singing.

Yeah.

Just something that I didn't phrase quite the way I thought I'd phrased it.

I'd go back.

Like if I'm singing something now, like when we're in a, before a show, when we're in the dressing room, we'll sit down and play guitars and sing old songs and stuff. And, and, I'll think that I'm singing it the way I remembered singing it. Then if I go back and listen to it, I'll realize that I'm singing it completely different.

Do you think you're a better singer now? I think, I hope so. Well, I don't know. I hope so.

Different, I guess, is a better way to put it.

I think probably just my voice, hopefully my voice has matured a little bit over the years. I go back and listen now and just think how much of a kid I sounded.

Hang tight. The Bobbycast will be right back.

Number two, Lone Star releases Amazed. On March 22nd, 1999, the country music group Lone Star released their iconic song, Amazed. And there are two main reasons it landed so high on this countdown. First, the success of the song itself. Amazed didn't just do well. It checked boxes that almost no country song ever gets to check. In 1999, it spent eight weeks at number one on the country charts.

which at the time was one of the longest runs any country single had seen in decades. That alone would make it one of the biggest country records of the year and the reason to put it on this countdown. But the success didn't stop there. As the song kept growing, it crossed over into other formats, and it just kept winning.

It reached number one on the Billboard Hot 100. That's all genres. Making it the first country song to top that chart since Islands in the Stream in 1983's from Dolly and Kenny. That gap from 83 to 99 tells you just how rare this was.

Country songs didn't do that in the 90s.

Not without the artist or the band completely changing the sound and the production of the song.

Amazed didn't change.

The same song that dominated country radio ended up competing directly with pop and adult contemporary releases, also climbing to number two on the AC chart. And by that point, it wasn't just a genre hit, It was one of the most recognizable songs in the country, period. I was talking to Richie McDonald, lead singer of Lone Star. I asked him if he had any idea how big this song would be.

Looking back and thinking how that song was pitched to us over at B & A Records in a song meeting. The A & R department was just really passionate about it, and we kind of got on board and No, we never had any idea. Once we recorded it, we thought it was a very passionate song, a song that, you know, people could relate to, a love song. We've always had great success with the ballads. You know, once we started climbing the charts, we had no idea what it was going to do, you know. Go on to be, shoot, I don't remember, eight or nine weeks on the country charts and then crossed over to the Pops. You know, at one point, there were so many different mixes of us amazed, Bobby. There were contemporary, hot contemporary. I mean,

I was driving home from Nashville one day, and I kid you not. I heard a dance mix, you know, the four to four. Every little thing that you do, I'm so in love. And that kick drum was just beating 90 to nothing. I'm thinking, well, I wonder where that came from. But, you know, it took on a lot.

Of its own.

It really did.

Whenever it's at the top of the pop chart and you have not only a bigger audience in the States, but I have to figure that the international audience was starting to grow.

Too, right?

Oh, absolutely.

Without a doubt, it opened up a lot of doors for us. And we went to Europe and, you know, a couple of times on just on the basically the strength of amazed. It's just crazy to think a song could, you know, could be so powerful, you know, not just here, but abroad.

When you're doing this song live, do you think about every show someone would propose during that song?

Well, you know, over the.

Years, we've had so many, so many fans and Just come up to us before the show, ask if they can come on stage and, you know, propose. Yeah, so what's happened? It's happened a lot. So I would imagine, you know, probably every show there's somebody out there that loves that song. And it's, you know, they pick their, you know, perfect timing to propose to their loved one.

I got to imagine there's a bunch of babies that are probably like, you know, 22, 23 years old now that were conceived amazed.

Without a doubt.

You know, I'm trying to think, you know, I took a brief hiatus from Lone Star a few years. And while I was out, the guys were out doing the process right. And Drew Carey said that he called Amaze one of the love making songs that he'd ever heard. And That was on The Price is Right, but that was 20 years ago. It's crazy to think, you know, how time flies, but a song like that, I don't know, it's just, it's timeless, really. I mean, people still come to the shows to hear that song, and I mean, it's just one of those classic songs, I suppose.

You heard Richie talk about the background of the song a little bit there, but let's dive into the details a little more to help understand how it all started. The song wasn't written by Lone Star. It came from some writers in Nashville that had written a lot of hits. Marv Green and Amy Mayo and Chris Lindsay. And Amy and Chris were a couple at the time. The couple said the song came straight out of that early, overwhelming stage of a relationship where everything about the other person feels larger than life. That's why the lyric doesn't overcomplicate the message. That's why it feels so relatable. Lone Star recorded it for their 1999 album Lonely Grill. When Richie McDonald sang it, the simplicity came through. His vocal doesn't

oversell the emotion. It does sound very sincere, though. It does sound conversational at the same time, just like he's trying to find the right words in real time. That delivery helped him turn it into something that listeners could relate to. The second reason that this song lands at number two on this countdown is because of all the awards that followed.

Man, was it successful.

In 1999, Amazed won ACM Single of the Year, an ACM Song of the Year, and it earned a Grammy nomination for Best Country Song. Those honors are important because it mirrored what was happening in the audience, and so the recognition was now coming in. And then there's the longevity of it. Years after its original run, Amazed continued to reappear, covered by artists all over the world. It became one of those titles you only have to say and everybody knows what it is. So many junior high dances were started because this song played as well. The level of success of that song put it near the top of 1999. From outside looking in, two more 1999 moments that almost made the countdown. You know, before we

wrap up, there's a few moments from 1999 that came close but didn't quite crack the final list.

Here's a few moments.

Number one, after years of building momentum, Sarah Evans broke through with her first number one.

1999, no place that far.

She co-wrote the song with Tony Martin and Tom Shapiro, two of the most reliable hitmakers in Nashville at the time. Tony's written 16 number ones, and Tom is credited with writing over 20. And pairing these songwriters with Sarah gave the song an extra level of credibility. This wasn't an outside pitch she happened to land. It was a statement song that she helped shape herself. Next up, Alan Jackson releases Under the Influence, which was an album of all covers.

At the time when major artists were focused on new material... radio singles, keeping pace with where the format was heading, Alan released an album made entirely of songs that were decades old. No original singles, no attempt to modernize them, just straightforward covers of classic country records that explained his career.

And that was unusual for someone at his level of career. Under the influence felt like it was him stepping aside from the race for a minute, just going, hey, I get the race, but this is what I care about. The song Pop-a-Top, originally recorded by Jim Ed Brown in 1967, climbed to number six on the chart. It Must Be Love, which was originally recorded by Don Williams in 1978, did go number one. The album made it clear Alan wasn't about chasing the moment. It was about pointing straight back to the music that shaped him. You know, Alan Jackson had so many hits throughout his career. I asked him how he decided which ones he would play during live shows when he was touring.

Well, over the years, I've tried to just bounce it back and forth with the audience and figure out which ones I feel like that they respond well to and also which songs fit together.

In a couple hours.

And I mean, it's tough.

It's tough.

I mean, I've had 60 or 70 singles, you know, that have been either one or five or top 10 hits. And I mean, I couldn't remember them all if you asked me. And it's, it's, it makes me feel really bad. Sometimes I'll see a fan out there holding up a sign of a particular song from 20 years ago that I hadn't sung in a long time. And, but every now and then they'll hold something up and I can, remember enough to sing the chorus or something for them.

That's kind of fun to do. It makes me feel bad. I know some people come to hear one particular song and you just don't get to do it for them. So I try to just pick the biggest ones and the ones that have affected the most people or that I enjoy as well.

And now let's do my 1999 non-country music edition. If you've been listening to this series, and I hope you have, we started way back in 1990. I have inserted something in each episode that is extremely selfish and is about my year of 1990 and then 1991. And then, well, here we are now at 1999. So I'm really saying this, if you missed any of the other episodes, and this is the first one that you're hearing, go on back, check it out. We started a long time ago, but my 1999 is the story of a kid in college who finds and uses and loves Napster.

That's right.

In June, 1999, an 18 year old college student named Sean Fanning launches Napster. His idea was simple. Instead of downloading songs from a company server, everybody shared their mp3s.

With each other. It was awesome.

You wanted a song, someone on the network probably had it. You just searched it up, clicked it, you downloaded it, it showed up.

It was free.

For the first time in history, Kid in Arkansas like me or in California or New York could get virtually any song ever recorded without buying a CD.

It was revolutionary. Also, it was cheap. Music was expensive.

You wanted one song, you had to go buy the whole album. A CD costs 15, 20 bucks. And then you got like one, maybe two good songs on the whole album. We were buying CDs and paying all this money for a song or two and the rest was garbage.

You know what we would do in the dorm?

We would just hit like the letter R, find every song that started with R and just download it. And then wake up the next day and it was all downloaded. You basically had every song that started with the letter R for free. Yeah, to a kid living in the dorm in college who had been spending a lot of money on music, Napster was amazing.

As I'm an adult now, I see all the faults and flaws with it.

But for a second, let's live in 1999. Because Napster gave all of us listeners instant access, unlimited choice, free music, discovery.

That was a monster.

And I would say of obscure artists, but sometimes they were just obscure in your regions. They could have been big in another part of America, but because the only way you could really get music then was going to the store. Some stores didn't carry all the music in certain areas that other stores and areas had.

It is wild. And man, it felt magical.

And also to record labels and artists felt like theft, which it was.

Look, now I see that. It wasn't good. It wasn't good. It should have never happened.

But if we can go back and put ourselves in 1999, I hated Metallica because they hated Napster. They were the anti-Napster movement. Metallica fought with Napster. Therefore, I hated Metallica. I looked it up. The fight started when an unfinished version of a song called I Disappear leaked online before it was ready to release. It was released Metallica discovered that it was spreading through Napster because people were sharing it that way. They sued. It was not a quiet suing.

That drummer, Lars Ulrich, delivered boxes of usernames to Napster headquarters and he demanded those users be banned.

Fans hated it. I was one of them.

Almost, I won't say overnight, but over about a week's time after this started, we were very anti-Metallica because they were taking away something that we felt like we earned.

Which we didn't.

We were just stealing art. It's crazy.

And the headlines were gritty rock stars versus music fans. I'm a little bit ashamed how mad I was at Metallica then because I didn't deserve to have this music for free. These people paid a lot of money to make this music and they needed to make money, right? But it still didn't mean at age 19 that.

That I understood exactly what was happening. I just wanted my free music.

A lot of artists privately agreed with Metallica.

I mean, some publicly did.

Dr.

Dre did join in with Metallica. And his thing was, if everybody gets music free, who pays the musicians? That's a very important question.

I agree.

There weren't a lot of people, as far as artists who supported Napster. I mean, Chuck D did from Public Enemy. And his whole argument was, The internet would free artists from record labels, and some artists were very smart with it, and they did use it as free promotion. The logic was, I'd rather have people hear my music for free than never hear it at all. That argument sounds incredibly modern now.

Both sides, you could argue, were right. Metallica was right that music sales would collapse. They did collapse. CD revenue got demolished. The traditional music business never recovered. But also, in a way, Napster supporters were also right because the internet opened doors for countless artists who would have never been discovered otherwise.

But yeah, you can't just take it and share it for free. There's got to be.

Some sort of monetary support that goes to the artists and the musicians and the creators. But man, the lawsuits piled up. The courts rightfully ruled against Napster. By 2001, Napster was dead. Man, it was a party of a three years though. And when Napster folded, the music industry celebrated. They thought they had won, but they hadn't. What Napster did though, is they made music just generally be better.

Meaning we had to buy those stupid CDs with 15 songs on it or 12 songs on it and two of them were good. We don't want to do that anymore. And the ability to just pick the songs that were good And that's what we did. And we would just download those. That made us then not want the bad songs anymore. And I think music got better because record labels realized if we were going to buy music at all, it couldn't suck. And then we started downloading music for $ 1. 99 or $ 2.

99.

It turned into Apple iTunes. And you wouldn't download the whole album because the whole album might suck except for two songs. So Napster was the signal. Fans were saying, one, we want the music digitally. And two, we want better music if we're buying a whole album. And then it all changed, right? Streaming, you got iTunes, then YouTube, Pandora, Spotify, Apple Music, iHeartRadio. Napster died, but the idea survived and it changed music forever. I mean, before Napster, artists made their money from album sales, CDs, physical distribution.

After Napster, artists.

Increasingly made money from touring and merch and and sponsorships and streaming. So the old model flopped, which it would have done anyway. And a new model kind of rose from the ashes. If Napster never exists, do we get iHeartRadio? Do we get Spotify? Do we get Apple Music? Maybe eventually, but probably not as quickly. And Napster taught an entire.

Generation, people like me, that, you know what? You should be able to get music immediately, digitally.

You want it on demand, you should get it.

And if you buy a whole album, you better not suck. Because you know what?

I'm not buying the whole album until I listen to every song. Don't get me started on YouTube, sticking a whole album on our phones. At least that was free. But 1999 was the year of Napster. The successful year of Napster. And then how Napster was successfully shut down years later. But man, two things that were awesome. Napster and Myspace. That's some nostalgic stuff right there.

Number one, one, one, one, one, one, one.

That's not an effect. That's my voice. Number one.

Okay, let's get to the final spot on the countdown. Shania Twain wins Entertainer of the Year. If there's one moment that really captures what country music looked like in 1999, it's Shania winning Entertainer of the Year. That's the award every artist strives for. It's not about one song or even one album. It's about the artist owning that entire year in every way. And in 1999, that award went to the biggest star of the late 90s who also happened to be a woman. That's why this ends up at number one. Because this moment wasn't just about one night or one trophy or one acceptance speech. It felt more like a snapshot of the genre right as the decade was ending. A clear picture of who had the attention,

the momentum, and the influence heading into the 2000s. By 1999, Shania Twain wasn't just having a good year.

She was everywhere.

By the time that award was handed out, Shania's path to that stage had already been years in the making. She spent most of the 90s steadily building from a promising new artist into the biggest name in the genre. Every album took her to a different level. And Come On Over didn't just cap that run, it blew it open.

By 1999, she wasn't chasing momentum anymore. She had the momentum. That's what made the night we're talking about itself so telling. She wasn't winning Entertainer of the Year in a quiet year. Against light competition, she was up against megastars, and the biggest male stars in country music at the time, who had dominated that category for most of the decade. Garth Brooks, George Strait, Tim McGraw, and no knock on those guys, it just shows you how impressive this win was. In fact, Shania Twain was the only woman to win Entertainer of the Year for the entire decade. That puts the moment into perspective. It wasn't just a great year lining up perfectly for her. It was a break in a long-standing trend.

The award had consistently gone one direction. In 1999, that direction finally changed. Her win reflected the scale of what she had built. Not just hit songs, not just big tours, but a presence that stretched beyond country music without abandoning it. She had become the face of where the genre was headed as the decade closed. And unlike some entertainer of the year wins that spark debate, trust me, they always do.

Some people are always upset.

This one didn't.

It made sense given the year she had, the crowd she was drawing, the reach she achieved. The industry wasn't taking a risk by giving her that award. It was acknowledging the reality of what was happening. That's why this stands as the number one moment of 1999. Because Shania winning Entertainer of the Year wasn't just about one artist having a great year. It marked a turning point. It showed who the genre had rallied around, who audiences were following, and how far country music had moved by the end of the 90s. That win didn't just close out the year.

It closed out the decade. Just a few years after she took home the Entertainer of the Year award, Shania was famously diagnosed with Lyme disease, which really impacted her career for several years in the early 2000s.

And I was talking to her about that.

I had Lyme disease.

I got bit by a tick. And, you know, Lyme disease can really get to your neurological system. And all the testing that I did, finally, because the vocal cords look normal from in a regular exam, but I've got slight atrophy on both cords. The nerves are damaged in there. And so I had to get five long needles. You get five long needles into your larynx and then they read your nerve activity. Yeah. And so I've got a bit of etching on both sides and it's really, really makes it really tough. I do a lot of vocal physiotherapy, basically.

Wow.

So that's a lot of warm up then before you go out.

Well, I'm trying to get the warmup down right now. I need about an hour and a half to warm up and I can't do any spontaneous singing. Like if I, if I was to sing like right now, I would sound like a dying cow. And that's really a bummer for me. Cause sometimes I'm in a club or whatever. And I feel like, you know, I just want to get up and sing where I want to do karaoke and, you know, get into the whole thing, but I could really damage myself if I did that.

Wow.

So, um, and I don't want to damage myself. I don't have nodules or anything that, you know, the typical singers have. This is from a Lyme's Lyme's disease. It's, um, nerve damage and it's really a bummer i'm stuck with it for the rest of my life but so it just takes a lot of work it's like a permanent.

Injury yeah it's got to be weird too just even singing knowing you have a lot of friends that are professional athletes and like that's it they've torn muscles hard but they say even the mental part of it is so hard because they don't even want to press on it because they're like what if even though they've done all the proper what if it.

Gives out and it is like that like if i don't warm up and really prepare it is i always do refer to it like a knee like a And you never know when that knee is going to give out on you. And that happens to me when I'm singing. Like I wouldn't be able to be an opera singer, for example, because, you know, but because I'm running around and I'm, I can ad lib and I can, I can work with it. I can, I can manage it.

And I'm just so determined.

Like I couldn't sing for a long, long time.

And yeah.

I could barely yell out for my dog. It's really, really, because the air escapes from the, you know, it's very technical, but I was just really determined to get to the bottom of it and find out what I could do about it. And little by little, I realized that I could do this. I could do it again. So now I'm not going to give up now. You know, it takes a lot of work. I have to say it's a lot of work and I do get discouraged some days.

Like an athlete with an injury, you do worry, is it going to give out on me when I'm on stage? Is it going to, Is it going to be there for me when I need it? But I feel really good just talking about it too. That helps me psychologically with it. And I accept it. It's just part of who I am now.

That'll do it for our top 10 moments in country music from 1999. From massive crossover hits to artists reshaping what the genre looked like, it was a year that left a real mark as the decade ended. If there's a moment from 99 that didn't make the list but sticks with you, feel free to share it. Thank you for hanging out with us for this episode and for the entirety of the 90s podcast.

If you're just hearing this, we did all the years. 90, 91, 92.

We did 93.

Then we did 94, 95. And then six. We did 97. And then we did 98. And now we're here.

We did all the years. So go and check it out. So thank you for listening to this series. Thank you for being a fan of country music. And we hope you love the 90s as much as we do. You can follow us on socials at The Bobbycast. Thank you for listening.

And we will talk to you hopefully soon. Goodbye, everybody.

Love this episode of The Bobbycast? Subscribe on iHeartRadio, Apple Podcasts, or wherever you listen to podcasts.

And now time for the credits for this series. Thank you for listening. Written by me, Bobby Bones. And kickoff, Kevin O'Connell. Quality control by Mike D.

Which means.

He listened to every single episode and made little notes about what we could do better, either in production or things I could say better or things we missed out on.

So shout out Mike D.

And fact checking, Abby Anderson, who listened to every episode and chased down every fact and sent many notes back going, the fact that you said is not correct. You should change it to this. Therefore, we did. So thank you very much, Abby. Thank you very much for listening. and check out the whole series. All you have to do, well, you're here, so search for the rest of them. All right, thank you, everybody.

Thanks for listening to a BobbyCast production.

Country Music in the 90’s: The Year is 1999

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