Jon Brennan reflects the sustainability of ageless country stardom at a crossroads

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Former MTV Real World cast member and world-traveled 30-year veteran country singer Jon Brennan has picked up far more Uber passengers from the Grand Ole Opry in his Chevy truck than the number of times he's stood in the Opry's legendary circle.

Brennan, 49, retains a youthful optimism about his return to Music Row. He's preparing to work on music with longtime friend and Grammy-winner Shooter Jennings, plus he believes he still strongly appeals to country fans between the ages of 45 and 54.

This story, one of three Tennessean features on artists left on the fringes of country music's latest evolution, examines how country's potential growth past its older fanbase impacts Brennan and artists like him.

Jon Brennan poses for a portrait outside of the Grand Ole Opry House in Nashville, Tenn., Thursday, Jan. 18, 2024. Brennan, who was a cast member on MTV’s The Real World in the 90s, is continuing to focus on his music career and driving for Uber.
Jon Brennan poses for a portrait outside of the Grand Ole Opry House in Nashville, Tenn., Thursday, Jan. 18, 2024. Brennan, who was a cast member on MTV’s The Real World in the 90s, is continuing to focus on his music career and driving for Uber.

Country music's radio, sales charts and touring data say it's currently a younger man's game.

"Every day I have to contend with the fact that I don't have as many social media followers as Bailey Zimmerman -- or even many ninth graders," jokes an undaunted Brennan.

"I was country when country wasn't cool and a reality TV superstar before social media."

Success defined by more than musical trends

Country music's 1990s era created tropes that will perpetually define the genre.

Between Aug. 1980 and Dec. 1992, seven country acts -- Alabama, Clint Black, Brooks & Dunn, Garth Brooks, Billy Ray Cyrus, Alan Jackson and George Strait -- saw stardom via consecutive hit singles that allowed one of them to have the genre's No. 1 song roughly every other month for that 12-year duration.

Owensboro, Kentucky native and lifelong country fan Brennan moved to Music City and started his first year at Nashville's Belmont University.

When in his first year there in 1991, Brennan was failing algebra. Also, he was being heavily pursued by MTV Real World co-creator Mary-Ellis Bunim to be a "fish out of water" cast member of the Los Angeles-based second season of the program.

The reasoning? Cyrus' platinum-seller "Achy Breaky Heart" spent 30 weeks at or near the top of Billboard's country and pop charts between April and December 1992. It sky-rocketed Cyrus and the genre to crossover renown comparable to Kenny Rogers and Dolly Parton in 1983.

Post-Real World, between 1993 and 1998, Brennan was affiliated with artist manager Ken Stilts (The Judds), producers like Scott Hendricks (Alan Jackson, Brooks & Dunn, Blake Shelton) and James Stroud (Clint Black, Tracy Lawrence, Tim McGraw) plus was signed, then dropped by Capitol Records and represented by Garth Brooks' first mainstream talent booker, Joe Harris (until his 1996 passing).

Brennan arrived in Nashville at 18. By 23, "ten-year town" logic said that he needed to wait until he was 28 to be seasoned enough to have success like that of Trace Adkins, McGraw and Shelton.

Among the many things that Brennan did between his Nashville stints included touring Uganda as a Christian missionary and leading a children's choir.

Jon Brennan, while busy at work as a missionary in Uganda. 2010
Jon Brennan, while busy at work as a missionary in Uganda. 2010

" I -- and many others -- were raised on were still-popular songs that touched on every emotion and inspired the world to want to live a 'country' lifestyle familiar to hard-working, middle-income American people."

'stubborn straight shooters...comfortable with the position they're in'

Acts including Jason Aldean (46), Dierks Bentley (48), Lee Brice (44), Luke Bryan (47), Kenny Chesney (58), Tim McGraw (56), Darius Rucker (57) and Blake Shelton (47) have all achieved No. 1 status in the past five years and still attract sold out crowds to venues with capacities from 5,000-50,000 people.

Brennan does not believe he can likely catch up to Kenny Chesney's near three-dozen No. 1 singles. However, mirroring veteran artists like Randy Houser or Joe Nichols -- both experiencing success of late -- is a more feasible goal.

In an April 2023 Tennessean feature, Nichols, like Brennan, was described as a "stubborn straight-shooter whose greatest driving desire is to achieve country music industry success comparable to names he counts as mentors, like George Jones and Merle Haggard."

Jon Brennan poses for a portrait outside of the Grand Ole Opry House in Nashville, Tenn., Thursday, Jan. 18, 2024. Brennan, who was a cast member on MTV’s The Real World in the 90s, is continuing to focus on his music career and driving for Uber.
Jon Brennan poses for a portrait outside of the Grand Ole Opry House in Nashville, Tenn., Thursday, Jan. 18, 2024. Brennan, who was a cast member on MTV’s The Real World in the 90s, is continuing to focus on his music career and driving for Uber.

"Like A Cowboy" vocalist Houser added to the Tennessean in Jan. 2023, "I'm not some new young prize-winning mule trying to make my way... I've been in the trenches, risen through the ranks, and am not going away."

'I Ain't Done Singin' Yet'

Brennan's goal is to achieve regular mainstream radio airplay while being a regular performer on the Grand Ole Opry.

Alongside driving for Uber, Brennan works with Joe Kelly at independent distributor CDX Nashville. CDX doubles as his current label, where his songs are slowly rising up the independent charts.

In July 2022, his cover of John Conlee's 1983 hit "I'm Only In It for the Love," spurred the veteran star to ask Brennan to join him on stage at the Opry.

Not content with guesting with Conlee, Brennan would like to make regular Opry appearances as a solo act.

As a child, Brennan's father, who died in 2019, watched the Opry on television with him and spoke about seeing Johnny Cash at the Ryman Auditorium.

An audience that would watch him there or at any significant number of pinnacle-level Nashville stages still exists.

When asked about attendance data for recent editions of the Country Music Association's yearly CMA Fest event, Catharine McNelly, the CMA's vice president of communications, highlights that festival ticket purchasers aged 45-54 are growing two and one-half times faster than those aged 18-34.

Alongside his still-constant pursuit of country stardom, Brennan has also launched the "Getting Real with Jon & Beth" podcast, where, alongside fellow Real World veteran Beth Stolarczyk, he's offering a "nostalgic insider's perspective on reality TV, music and pop culture."

Jon Brennan poses for a portrait outside of the Grand Ole Opry House in Nashville, Tenn., Thursday, Jan. 18, 2024. Brennan, who was a cast member on MTV’s The Real World in the 90s, is continuing to focus on his music career and driving for Uber.
Jon Brennan poses for a portrait outside of the Grand Ole Opry House in Nashville, Tenn., Thursday, Jan. 18, 2024. Brennan, who was a cast member on MTV’s The Real World in the 90s, is continuing to focus on his music career and driving for Uber.

The only true story similar to Brennan's life at 18 is his relentless passion for achieving success by his own standard.

"I'm young at heart and still going after all of my most super-meaningful goals. I can only pursue those goals by being comfortable living the kind of life and making the kind of music I've always loved."

This article originally appeared on Nashville Tennessean: Jon Brennan still holds out hope despite career lull, industry trends