On a hot summer evening in a Nashville venue, Jon Brennan walks onstage. He faces the audience, tunes his guitar, and fixes the microphone to the perfect height.
After adjusting his cowboy hat, Brennan puts his fingers into position on the guitar strings and glances back just long enough to make eye contact with his drummer, letting him know that he’s ready to go.
The count-off begins: 1, 2, 3, 4 …
As Brennan and his band play, the music surrounds the crowd.
Finally, Brennan steps up to the mic and does what he does best: He sings.
A Country Singer Is Born
For as long as he can remember, Owensboro resident Brennan, 49, has been singing. His love for country music came from his late father, Dan.
“He was always into Willie Nelson, Waylon Jennings, Johnny Cash and George Jones,” Brennan recalled. “When I was old enough to drive around in the car with Dad, he would always have country music playing. That’s when I started to sing along.”
Brennan’s favorite band was Alabama, and he would blast the group’s song “Roll On (18 Wheeler)” while singing along at the top of his lungs. That’s when his mom, Joy, who sang in the church choir, realized that her son could really sing.
When Brennan was just 8, he began singing “The Star-Spangled Banner” at his brother Buck’s baseball games. Dan knew someone with the NBA’s Phoenix Suns, and Brennan once sang the national anthem before a Suns game.
“That was so cool,” Brennan said.
In high school, Brennan discovered Goldie’s Best Little Opryhouse in Owensboro. During open-mic night, Brennan signed in and sang with the house band. “That’s where I really began to develop as a performer,” he said.
Brennan became an attraction at Goldie’s, and proprietor Goldie Payne began to pay him. “Every Friday and Saturday night, that’s where I was. I wasn’t out causing trouble. I was at Goldie’s on the weekend making gas and insurance money because I had a truck,” Brennan said. “People would come and pay to hear me sing.”
The 17-year-old Brennan decided he was going to make singing country music his career. He chose to attend Belmont University in Nashville while he tried to make it big.
That’s when MTV came calling.
MTV Cowboy
In the early 1990s, MTV was huge, and its reality show, The Real World, was even bigger, especially since it was the only program of its type airing at the time.
When Brennan was in Nashville, a scout for the show approached him and asked, “Are you a singer?” Brennan replied, “Dude, you’re in Nashville. Everyone’s a singer!”
The scout was looking for someone to be on the show. Brennan hadn’t heard of it, wasn’t impressed with MTV, and told the scout he wasn’t interested.
But the scout was undeterred. Finally, Brennan agreed to fill out paperwork for the producers “so he’d leave me alone.”
The producers asked him again to be on the show. He said no. They asked another time, and once more, Brennan said no.
It wasn’t until Mary-Ellis Bunim, a creator of The Real World, said something to Brennan that eventually changed his mind: “Jon, have you ever thought about how being on the show could really help you with publicity and spark your country music career?”
He turned her down once more.
The next day, she called him one final time, saying that he would be perfect for “Season 2: Los Angeles.”
At the time, Brennan was failing college algebra and missing home. “It just started sounding cool,” he admitted about appearing on the show. He laughingly added, “Then I thought, ‘How am I going to tell my mom and dad that I’m considering moving to California and being on MTV?’ I might as well tell them I was joining the circus.”
For 20 weeks, Brennan lived with roommates in L.A. on The Real World. Afterward, he became a country singing sensation, opening for acts such as Alabama, George Jones, Tim McGraw and Eddie Rabbitt. He also performed in countless shows as the main attraction. Brennan was flying high.
Then the perfect storm happened that would derail his career.
His recording deal with Capitol Records fell through when Capitol decided to back up-and-comer Trace Adkins. Brennan’s contacts at Capitol assured him that he would get offered another record deal through a different label.
One night, his manager (now deceased) called him while drunk and cussed him out. Brennan, a lifelong Christian, fired him. Shortly after that, Brennan’s booking agent, whose client list included Garth Brooks, passed away.
Brennan thought that, once everything had settled down, he would get new representation and then a new record deal.
But the business had changed. “When I got to Nashville, they said, ‘You’re really good, but you’re just kind of young,’ ” Brennan said. “Fast forward 10 years later, when I’m 28, and they said, ‘Now, we’re looking for really young acts.’ I’m like, ‘You gotta be kidding me.’ ”
Brennan decided to take a break. He began playing music for a church and thought it would be temporary. He ended up becoming a youth pastor, spending years in East Africa as a missionary and working in the ministry for nearly 20 years.
Then MTV came calling … again.
Launching a Comeback
In December 2020, producers of The Real World Homecoming: Los Angeles wanted to unite the original cast and film them catching up over a couple of weeks. Brennan was still in touch with all of them and was able to help make it happen.
“I saw this as a second opportunity to have a lot of exposure really quickly and remind everyone that Jon Brennan still exists,” he said. In August 2021, the reunion was filmed with all but two roommates.
Brennan had already been thinking about the road he hadn’t continued traveling—that of country music—a few years before, when his dad had passed away.
“When he got sick, I started to think, ‘I’m getting older. I need to do this,’ ” Brennan said. Aside from launching a comeback because of his dad’s influence, Brennan is doing it for himself: “I miss it.”
Before Homecoming began filming, Brennan reached out to some friends, including Shooter Jennings, the son of Waylon. Jennings connected Brennan with Grammy Award winning songwriter Aaron Raitiere—who has written and co-written countless songs, including the Grammy-winning “I’ll Never Find Love Again,” sung by Lady Gaga and Bradley Cooper in the movie A Star Is Born.
Raitiere and Brennan collaborated on some songs, including the one that also bears the name of his most recent EP: I Ain’t Done Singin’ Yet.
After filming Homecoming, Brennan recorded the vocals and released his EP. He’s now an independent artist with CDX Records, and his single “I Ain’t Done Singin’ Yet” has been steadily climbing the MusicRow Chart, a country music chart published each week by MusicRow magazine that measures success according to a song’s radio play.
Brennan refers to it as his “signature song.”
As part of his comeback, Brennan has played concerts, become an ambassador for St. Jude Children’s Research Hospital, and started a podcast called Getting Real with Jon and Beth co-hosted with his Real World roomie and longtime friend, Beth Stolarczyk. He’s also released a new song, “True Story,” to Positive Country Radio.
One of Brennan’s dreams has already come true—he’s sung at the Grand Ole Opry.
That came about in July 2022 after Brennan recorded the John Conlee hit “I’m Only In It for the Love.” A friend connected to Conlee played Brennan’s version of it, and Conlee loved it. That was on a Tuesday. Conlee told the friend that Brennan should sing it with him when he was performing at the Grand Ole Opry that Friday and Saturday.
Brennan jumped at the chance.
Brennan would love to be a household name as a country music entertainer. He hopes to have a number one hit song. He wants to tour again.
“I’ve heard it all—‘You’re too old. You’ve missed your prime. You’ve missed your chance,’ ” Brennan said. But he’s still determined to make it. “Here’s the bottom line: I’m making better music now than I ever have. Frankly, I’m singing better than I ever have. And I still have the passion in my heart to do this.”