The Cadillac Three’s Best + Worst Gigs, Parties + Celeb Stories

The Cadillac Three‘s best after-party involved Jake Owen and Jack Daniel’s bottles to the ceiling. The worst spilled into the streets of London and ended with someone on their team getting his jaw broken.

Jaren Johnston, Kelby Ray and Neil Mason are looking back on their career as a country trio in the most Cadillac Three kind of way. It’s the best and worst moments from their time in Nashville, on the road and on a golf course with Florida Georgia Line, when someone on the crew bet Johnston he wouldn’t ask the crowd a not-so-sneaky dirty question.

Spoiler alert: The frontman and guitarist won that bet.

Few country bands have done more during the pandemic than TC3, and the hard work has paid off with a nomination in the ACM Vocal Group of the Year category — their first ever. In February 2020, they dropped the Country Fuzz album and started a tour of the same name in Europe, until the pandemic shut them down. Last summer, they launched a series of livestream concerts to help feed disadvantaged families who had distance learners at home for the first time.

Then, in October, came the Tobacco and Sweet Tea album. No, it didn’t notch a radio hit, but that wasn’t the point. “This last week I’ve gotten more messages from people at radio thanking us for this record. That they needed this record,” Johnston told Taste of Country last fall. “Not that they’re gonna play it, just genuinely nice messages about how good they think the record is and how fun it is and how much they think country music needs it, which is so ironic, because we’re probably not gonna get much play on that.”

Even though the Cadillac Three have made friends in radio and throughout the industry, the nomination was a surprise. It’s also a chance to look back at how they got here. The following answers have been edited for clarity.

Best Gig:

Mason: The best? I dunno, it probably goes back to the Ryman [Auditorium in Nashville]. I just remember us just walking on stage at the Ryman … The crowd was just like going crazy and they were all on their feet and so we walked to the center of the stage and all like hugged each other and were standing there. It was just one of those big hometown moments … one of those things you’ve been dreaming about since you were a kid actually happening.

Johnston: Normally you cry after the show, and we cried at the beginning [laughs].

Worst Gig: 

Johnston: One comes to mind, and it was in Greenville, S.C., at the Handlebar. And there was nobody there. We were opening for a band called Don Chambers and Goat and no one showed up at all. Even the sound guy left the room, so we all switched instruments and started playing jazz fusion.

Ray: True story.

Johnston: Don Chambers walked out after the show and offered us $50 and we took it, and then Neil and I took shots and I went and puked in the trashcan. Then we left.

Mason: I think that is the worst. I thought you were gonna go with the FGL show on the golf course.

Johnston: That’s one of my best shows [laughs]! The Dick’s Sporting Goods Open. At the end of it, some of their crew guys had dared me to say “How many of y’all like Dick’s?” And you know me [laughs] … He said he’d give me $100, and so I said, “How many of y’all like Dick’s?” and raised my hand looking for it. The crowd loved it, but I guess the owners didn’t like it very much, so still to this day I can’t walk into a Dick’s Sporting Goods anywhere.

Worst Celebrity Interaction:

Ray: I would say worst celebrity interaction that tried to happen is we played with Dwight Yoakam, and right when we got done playing, Jaren was like, “I’m gonna go run to his bus and say ‘Hi’ to him. But Jaren walked out there and like … dust. He didn’t give a damn about meeting anybody.

Johnston: They had set it up, like his manager had talked to my manager. I’m standing over there like a big fan waiting for him and no Dwight. And I hear the bus crank up, and a big white Prevo, vroom, gone.

Best Celebrity Interaction:

Johnston: We were drinking at the Rainbow Room in LA with Shooter Jennings and his ex-girlfriend, Drea De Matteo. Then we kind of realized we were sitting in the same group, like literally across the table, from Scott Weiland from Stone Temple Pilots, one of my favorite bands of all time. We got talking a little bit, not really. But that was a fun, really cool interaction. Also Daniel Johns from Silverchair, we smoked a joint with them backstage at the Avalon in LA.

Worst Song Idea:

Johnston: I did write this song with Cale Dodds and Corey Crowder. I had this title in my phone forever: “Where Do I Go From Beer?” [sings] ”Where do I goooo from beer?” 

Best Song Idea: 

Mason: I remember the first time I heard “Raise ‘Em Up,” just the amount of ways that [Jaren] kind of turned the hook in that one is a really great one. Just because you hear that title and you think it’s gonna be one thing and you get that in there, but it’s not really what the song is about at all. There’s great titles, but unless the song is good, it doesn’t really matter.

Best After-party:

Johnston: The best ones were on that Jake Owen Days of Gold Tour. We had some really fun nights on those. Jake would always turn the backstage into like … you’d feel like you were in a different place than you were, getting ready for the show. There was one night, there was a stack — taller than my wall — of Jack Daniel’s bottles. Liters of Jack Daniel’s just stacked on top of each other. And we would just get after it.

Worst After-party:

Johnston: London. We had an after-party after the show at the Lexington and we got into a huge fight, a street brawl, in the street afterwards. That was definitely the f–kin’ worst [laughs].

Mason: Yeah, that was bad. Our tour manager got his jaw broken … and it was such a good night until then.