Country singer-songwriter Bailey Zimmerman’s rise to fame didn’t start in music; it started in the world of custom cars and trucks. In 2019, Zimmerman began his #TruckTok videos on social media. The first video he posted focused on him adding a lift kit to his GMC truck, which, he says, got him somewhere around 70,000 views. 

“It was kind of all very random,” he tells me over Zoom. 

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Zimmerman fell down a TikTok rabbit hole, posting videos of his truck, getting views and comments, building an audience. “I really loved putting my truck out there,” he says. “People were loving it. I was meeting a lot of new people by doing that.”

He even joined a truck club, and for a year and a half, he traveled throughout the country and met up with other customized truck lovers. During his occasional bouts of drunk karaoke, friends would compliment Zimmerman on his voice, but he never took it seriously. It wasn’t until he was singing along to Black Stone Cherry’s “Stay” one day that he realized that maybe his friends were on to something. Then he decided to record himself singing it and post it online

That’s when Gavin Lucas entered the picture. 

Lucas’ dad drove Zimmerman’s school bus in his hometown of Louisville, Illinois, and approached him about getting together to play music. “Gavin was like, ‘Hey man, I don’t really tell a lot of people this, but I’ve been writing songs and I’ve written them for a long time. And I know I play guitar and your voice is really cool. Would you want to sing and hang out and like, listen to my songs?’ I’m like, heck yeah man, I don’t know how to play guitar, but I would love to try to listen…And we started hanging out…a couple weeks go by, a month goes by and I’ve been watching him write, I’ve been just trying to like, champion him almost. Like, I still didn’t really think of me being a singer.”

After a couple of months, in December 2020, Lucas and Zimmerman wrote their first song together and posted it on Zimmerman’s TikTok account. Lucas told him that if they got some views, they’d go and cut it at a real studio. The next morning changed his life, Zimmerman says. The video had more than one million views. 

That song was Zimmerman’s debut single, “Never Comin’ Home.” 

(Credit Isaac Mason)

“I quit my job that same day,” says Zimmerman. “I started working on that and that’s kind of how I came up, man. I just tried. And then every single thing I’ve done since then has been, I have no idea what I’m doing. I’m just trying to sing really good and trying to write awesome songs that I love.” 

Since then, Zimmerman released his debut album, Religiously. The Album in 2023, which debuted at No. 3 on Billboard’s Top Country Albums Chart and became the biggest streaming debut across all genres. He then set out on his first headline tour with 30+ dates in North America and Europe, selling out every show. This year, he achieved his fourth consecutive No. 1 single on country radio with “Where It Ends,” following “Rock and a Hard Place,” “Religiously” and “Fall In Love.” 

Ending the year on a high note, Zimmerman performed at the 2024 CMA Awards and was nominated for “Best New Artist.” 

“Six months before I started singing, I remember asking my mom, ‘Hey, I want to move out and I want to get my own place…’ And she’s like, ‘You think you can afford to get your own place?  You can barely afford your truck.’ And she was right. I couldn’t afford nothing back then. Didn’t really have a plan, didn’t know what was going on… and now to not only be able to do music for a living, but to be looked at and acknowledged, like that is crazy. And it’s a great feeling too, because there are a lot of people behind the scenes who believed in it just as much as I did…it’s such a good feeling for everybody. It’s definitely a privilege…to be able to get recognized for all the hard work is yeah, unreal. And I don’t feel like I deserve it, but I’m very thankful.”

Here’s a day in the life of…Bailey Zimmerman.

Where are you?  Hollywood, Florida. I got a show where we are playing at The Hard Rock. Yeah, it’s gonna be fun. 

Time I woke up  I woke up this morning about 5:30 a.m.

Every day starts with  Marley Maye [my dog] and Pie. Pie is my new puppy that I just got. Nice. Yeah. So Marley and Pie. 

Breakfast consists of  I’m a massive Eggs Benedict guy. I love Eggs Benedict. I can do McDonald’s Chicken McGriddle. I just had a chorizo egg quesadilla this morning, which was unbelievable. So yeah, breakfast is one of my favorites.

To get going I always listen to  Probably Nickelback. “Burn it to the Ground” to be more specific. That or Zach Top.

I don’t feel dressed without  Air Force 1s.

Before I start working I must  Eat.

Currently working on  Everything, everything…music album, new tours for next year, the tour for ’26. Man, I’ve got another company called BZ Motorsports where I give trucks away and money with the trucks to help people out. And I do that all the time. So honestly, everything. I stay busy doing all the stuff. 

But I’d really love to be  If I had all the money in the world, I’d love to be at Cabo on the beach playing golf. 

Book I’m reading  Greenlights by Matthew McConaughey. And getting more into the Bible as well. 

I don’t know how anyone ever  Eats oysters. That’s disgusting. It’s absolutely disgusting. I don’t understand how you do that. Tastes like a loogie.

If I had to play one album on repeat, it would be  It would actually be a tie for Traveller by Chris Stapleton or Golden Hour by Kasey Musgraves.

The perfect midday consists of  Man, I love going on a cruise [in a car] during the middle of the day. Maybe go get some lunch, go out to Mexican or something, and then honestly get back to the studio. 

Bailey Zimmerman performs onstage during The 58th Annual CMA Awards at Bridgestone Arena on November 20, 2024 in Nashville, Tennessee. (Credit: Theo Wargo/Getty Images)

To help get through the day  I drink chocolate milk when I’m not supposed to. That’s a real thing. That’s one of the things that I do during the day to help me get through. I would say that and allotted breaks with Marley and Pie. Breaks and chocolate milk, you know? I got dirt bikes on the property. So ride dirt bikes, play with Marley, swim in the pool…and then get back. 

Not a day goes by without speaking to  Wish I could say God, but I can’t say that. There’s days that go by where I don’t. Tracy Martin…not a day goes by without talking to Tracy Martin. And that’s the president of Core Management [The Core Entertainment]. And she is one of my best friends. And we talk all day every day. My mom. I usually talk to my mom quite a bit too.

My daydreams consist of  Just honestly, the daydreams consist of, how do I blow more up in my show? What else can I do in the show to have more fun? And then I also think about what truck do I wanna build next and what car do I wanna build next? The beach a lot of the time. I’m like, man, I could definitely just go live in a shack on the beach if I never wanted to do this. You know? That’s definitely a daydream, you know? And food. I’m skinny, but man, I’ll put it away. 

I’ll always fight for  My faith. I’ll always fight for my faith. 

Currently in love with  Italian food. I’ve been eating so much Italian food every night. Chicken Alfredo or Bolognese. Yeah. And Caesar salads. Woo. I’ve never experienced the amazingness of a Caesar salad until the other day. And now it’s all I want. I’m like, dude, Caesar freaking salad.

Hoping to make time to watch  There’s a couple of Netflix shows that I’ve really wanted to watch. I just can’t remember the names of them. I really wanna take the time to watch this show called Capone. I’ve been seeing it all over TikTok. I would say also I’d like to make some more time to watch more football at the bar, preferably with my boys.  

To help get through the night  Leave some lights on because when I wake up and that chair is in the corner of my room and it kind of looks like something’s in there…

When I think about tomorrow 
I’m excited. Hopefully, I get the chance to live tomorrow, but I also don’t think about tomorrow that much anymore other than work, you know, having to look forward into the future on that stuff. But as far as life goes or decisions or things that I want or whatever may be, I really try to live in today so I don’t miss what could be tomorrow, you know? I feel like if I’m not watching today and looking today and I’m just daydreaming, then I’ll never be able to have a tomorrow.

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