When Vincent Mason took the stage for the first show of his There I Go headlining tour in late January, the Kansas City crowd’s response to “Damned If I Do” clued the country singer-songwriter in on the draw of his gritty, rock-oriented hit.

“The way the room popped was really cool,” he remembers. “I was like, ‘Oh s–t. That’s the new one. That’s the song people are coming to hear.’”

Born and raised in Roswell, Ga., the 25-year-old grew up inspired by the music of John Mayer, and later, Parker McCollum. As a college student at Nashville’s Lipscomb University, Mason began posting music to TikTok during the COVID-19 pandemic. In early 2024, he fused his raw lyricism and country stylings into his acoustic-leaning ballad “Hell is a Dance Floor.” Three months after the song’s independent release, thanks to its viral momentum from streaming and TikTok, Mason signed a record deal with Interscope Records/Music Soup and subsequently partnered with UMG Nashville/MCA (more recently, he’s releasing music through MCA imprint Lost Highway in partnership with Interscope/Music Soup).

Two years after joining the label roster — during which he released songs including “Speak of the Devil” and “Wish You Well”  — Mason’s career is now ascending to new heights with “Damned If I Do.” The track debuted as his first Billboard Hot 100 hit in mid-May and has since peaked at No. 77. “I’ve been putting out songs a little under three years now, posting to TikTok,” Mason says. “This felt like the first since ‘Hell is a Dance Floor’ that I knew, ‘Alright, this one’s got some momentum.’”  

Vincent Mason Aaron Sinclair

He crafted “Damned If I Do” at the start of 2025 alongside co-writers Lauren Hungate and Jacob Hackworth; and with a deepening interest behind the boards, he earned a co-producing credit too.

“[Hackworth] sang this melody and I was like, ‘That should be the guitar line,’” Mason recalls. “At the time, I hadn’t gotten into the production side the way I am now — it was a whole different side of things for me. In the studio, we had the band play it a few different ways. Telling them how you want the song to be was a little nerve-wracking at first because they are some of the best players in the world, but we made it feel like something new to me.”

The song’s layers of guitars, bass and pedal steel — added with Mason’s heart-torn vocal — lay the foundation for the angsty nature of the track, particularly when combined with lyrics like “You ain’t here, but you won’t leave/ You’re everything I ain’t over.”

“Damned If I Do” was officially released mid-July of last year, but Mason first teased it weeks earlier, releasing a snippet of an unfinished mix to TikTok on June 24, followed by a finished-mix snippet on the same platform July 3. According to Red Light Management’s Matt Musacchio, who reached out in 2022 after discovering Mason in Apple Music’s pop section, the song’s initial growth was buoyed by “TruckTok,” a TikTok community that allows truck and truck culture enthusiasts to share their passion through TikTok videos.

“It’s always interesting to see what kind of niche audience picks up audio and runs with it,” says Musacchio. “We saw a lot of truck videos early on that used this audio — it’s definitely on the angstier, rock side of what Vincent does, and that plays into the truck community, especially.”

In November 2025, Mason released his debut album There I Go (which included “Damned If I Do”) and embarked on several opening tour slots. But when he launched his headlining There I Go tour on Jan. 22, he says the January-May run of shows proved to be a winning strategy.

“We had been opening tours and honestly, maybe not necessarily tours where the overlap was there; it maybe wasn’t our fans that would have heard the song,” Mason says. “I was like, ‘Oh, it streams well, but I’m not sure if people are liking it.’”

“It is a hard-hitting, more uptempo rock moment in his set,” Musacchio adds. “It’s not a departure, but shows a different side from a lot of his other material and it feels like a great evolution from ‘Hell Is A Dance Floor.’”

Performing “Damned If I Do” each night in his headlining sets further bolstered a streaming surge and TikTok usage of the song, all of which led to Mason making his late-night television debut on The Tonight Show Starring Jimmy Fallon in May.

“That consistent visibility on social and the live show, along with some of those tentpole moments, have kept the momentum going and allowed us to see it through to this point almost a year later,” Musacchio says.

Vincent Mason Aaron Sinclair

Another significant moment for Mason has been his languid, love-struck collaboration “Something To Lose” with fellow country-leaning artist and girlfriend Stella Lefty. Since debuting in mid-June as both of the artists’ second Hot 100 entry — Lefty’s Noah Kahan-interpolating “Boston” has taken off in the past few months, reaching No. 14 — the track has continued to climb as the couple has soared in commercial prominence in tandem.

“She wrote ‘Something To Lose’ and a few other songs in that first week of us hanging out and was like, ‘It’s kind of about you and me starting to hang out and talk,’” Mason says. “It’s cool to see that one working as well. That was the first real collaboration I’ve done. It felt like there was obviously a lot of natural synergy there.”

Looking ahead, “Damned If I Do” will impact country radio on July 13, while Mason and his team are making new music – such as his new song “What You Want” – with a wide creative lens. Mason credits it to his “newfound love for the production side of things, paying attention to mixes and pulling from different music that I’m inspired by. We’re blocking out significantly more time than I had last year for me to take longer on songs, go down different rabbit holes and even make different versions of the same songs.”

“I like the trajectory that we’re on,” he adds. “It feels like a natural step forward.”