Anytime we get the chance to catch up with one of our hometown celebrities, we take it! Visit Owensboro was so excited to chat with singer/songwriter/reality TV star Jon Brennan about his country music career, his experiences as a cast member on The Real World, and how the city of Owensboro shaped his successful path.
Brennan’s fame came early in life, as he made history starring as one of the cast members of MTV’s “The Real World: Los Angeles” at only 18. The success of that season would make The Real World one of the most popular reality shows ever created, earning Brennan subsequent appearances on a host of other MTV shows, such as “Road Rules All-Stars,” “The Challenge Inferno 2” and “The Real World Homecoming: Los Angeles,” which aired in 2021.
From a young age, Brennan had a dream of becoming a country music artist. After his experience on The Real World, Brennan toured extensively and made many appearances across the nation, garnering thousands of fans along the way. He opened for some of the biggest acts in the business–Alabama, Tim McGraw and George Jones, to name a few!
To this day, Brennan is making country music, and he released his new EP “I Ain’t Done Singin’ Yet” in 2021, which did very well on the country music charts. Right now, Brennan has a song out on country music stations called “True Story” – a song he co-wrote about his parents’ struggles as a young, married couple trying to get ahead. The song was #1 for multiple weeks at Positive Country Radio and has been climbing the mainstream country music charts ever since, currently sitting at #66.
“A music video for ‘True Story’ will be released soon–within a week, I am hoping,” Brennan said on March 14. “And I’ve shot another video for my song called ‘Alabama, Tennessee, Kentucky’ that will be released in the future.”
As for The Real World, Brennan said he’s started a weekly podcast with his fellow castmate Beth Stolarczyk called “Getting Real With Jon And Beth,” which is available to stream on all the sites and apps for podcasting (Apple, iHeart, Spotify, and all the rest).
Currently, Brennan is working on new music. In fact, he’s working with one of the biggest producers in Nashville right now, where he currently resides.
“I am writing songs and looking for songs to go back into the studio to record with Grammy-winning record producer Shooter Jennings. Shooter produces artists that include Tanya Tucker and Brandi Carlile, and he’s the son of country music legends Waylon Jennings and Jessi Colter.”
One of Brennan’s proudest moments of his career was when he was invited to sing at the Grand Ole Opry in June 2022 with fellow Kentuckian and Opry Member John Conlee. Brennan said his goal is to return to that stage as a performer.
Beyond the music, Brennan has spent much of his life dedicated to missionary work. While serving as a missionary in Uganda, he was able to baptize many people in the Nile River–a special highlight that he puts right up there with performing on the Grand Ole Opry stage.
And as for Owensboro, much of Brennan’s career in country music was kickstarted through his experiences in this city. He began singing at Goldie’s Opryhouse on Frederica Street–now home to Theatre Workshop of Owensboro–after his Garth Brooks cover was a huge hit at his Daviess County High School talent show. After shooting The Real World in 1993, the production team at MTV came to Owensboro to shoot a Mother’s Day special. Brennan even took the crew to Owensboro’s world-famous International Bar-B-Q Festival, now known as BBQ and Barrels.
“Owensboro shaped me greatly, and I miss living there,” Brennan said. “We are told when we are young to ‘follow our dreams’ and that you can ‘be anyone you want to be.’ And I’m putting that to the test. Do hard things. Try hard things. Go for it with no regrets. That’s why my first single was called ‘I Ain’t Done Singin’ Yet.’ One day, while living in Alabama, I realized I still wanted to sing country music. But I wasn’t trying anymore. So now I’m back in Nashville–trying, reaching for the stars.”