Conner Smith Enlists Hailey Whitters for a Metaphoric Game of ‘Roulette’: ‘I Knew the Song Was a Next Level for Me’

Conner Smith earned his first top 20 single when his swampy speedster, “Creek Will Rise,” worked its way to No. 12 on Country Airplay. Its torrid pace and pickup truck motif likely made more than a few listeners think of Garth Brooks’ “Ain’t Goin’ Down (Til the Sun Comes Up).”

But the follow-up — “Roulette on the Heart,” featuring a vocal assist from Hailey Whitters -— resembles a country classic from the other end of the energy spectrum, the Brad Paisley/Alison Krauss duet “Whiskey Lullaby.” Like that ballad, “Roulette” pairs a male and female solo artist in a Dobro-heavy piece built around a dark, fatalistic storyline. In “Whiskey,” the plot captures an alcohol-infused double suicide, fueled by broken hearts. Smith’s concoction, conveyed at a slightly faster tempo, leans on Russian roulette as a metaphor for risk in a relationship with a wild woman.

Smith didn’t have “Whiskey” in his mind when he created “Roulette” in early December 2022, but he sensed a significance about his work from the outset.

“When we wrote it, I knew the song was different,” he allows. “I knew the song was a next level for me. It felt like a song for me -— and it still does — that could last for a long time, in a way that I don’t think I’ve put out a song before. And so it mattered a lot.”

Smith had his then-girlfriend -— surfer Leah Thompson, whom he married on April 12 — in mind when he developed the “Roulette” title, which sprouted from the inherent danger in both single-bullet games of chance and extending love to another.

“When you’re in those [intense] relationships, the reality is you get married or you break up,” Smith explains. “You either find the person for the rest of your life or you shatter your heart when you fall in love with someone, and that game, in and of itself, is roulette.”

Smith brought the title up during a writing retreat at a Tennessee cabin owned by Thomas Rhett. He wrote two songs simultaneously, “Roulette” and the title track to his EP How It Looks From Here, shifting about every half hour from one writing room to the other. That is, it turns out, an ideal situation for him.

“I’ve been writing with him for a long time now,” says songwriter Mark Trussell (“Your Place,” “Good Time”). “What I’ve noticed is that he does kind of need to step out and step back in. It’s good for him creatively to take a break and come back. And then he comes back real fresh, and he can just pick up a guitar and spit out a whole verse. He’s really good at doing that.”

Trussell and co-writers Jessi Alexander (“Light on in the Kitchen,” “Chevrolet”) and Chase McGill (“5 Foot 9,” “Break Up in the End”) were all on board with “Roulette.” McGill developed a folky, foreshadowing guitar lick, and the group came up with a telling first line: “Picking you up’s like picking up a gun/ Your kiss is the trigger.” The story unfolded chronologically from there, each phrase underscoring the protagonist’s magnetic attraction to a romantic partner he knows could destroy him.

“This is definitely not your perfect, healthy relationship,” notes Alexander. “This is for the people that are playing with danger and mystery and a little bit of an unsettled relationship. And she’s a pistol.”

The chorus lifted the song’s energy, altering the cadence and the pace of chord changes to signal the arrival of the singalong section. “A lift doesn’t always have to be a melodic, high lift or a crash cymbal on the chorus,” Trussell says. “So in this chorus, the melody moves quicker and starts rolling a little bit more, and the chords slow down.”

Verse two focused on an intimate moment between them, mixing a half-dressed sexual inference with another “steel of a Colt” gun metaphor. Alexander had a leading role in that stanza’s tone. “I love provocative, I love edgy -— you know, shock value,” she says. “I’m the girl that put makeup sex in ‘Mine Would Be You,’ so I’m like, ‘Bring it on. Let’s do something kind of edgy.’ ”

The bridge spelled out the risk that the rest of the song implied. Again, they fashioned a subtle melody, using a variation on the last half of the chorus’ tune, maintaining continuity amid the lyrics’ tension. In the final chorus, Smith inserted an extra line — “Loving you, baby/ Is flipping off the safety” — continuing the firearms symbolism in a unique way.

“The action of that elicits an emotion of danger, and I think it’s cool because that is the game of love,” says Smith. The characters are “obviously taking it to a much deeper and darker place. Anytime you step into a relationship, you realize that you are flipping off the safety of your heart.”

Smith turned in a lead voice, and Alexander provided harmony for a demo that Trussell continued to work on after the session ended, using mostly acoustic instrumentation, including a resonator guitar.

Just days after writing it, Smith sang it during a WDAF Kansas City concert at PBR Big Sky on Dec. 7, 2022. A rowdy cowboy bar wasn’t the best venue for an unknown ballad — patrons mostly ignored it — but when Smith was done, fellow artist Whitters leaned over to compliment him on a “brash” song with an uncommon level of vulnerability.

“I thought it was cool hearing it from a guy,” she says. “Instantly, as a chick, I connected with it.” 

Smith’s team had high hopes for “Roulette” when he recorded it in February 2023, with producer Zach Crowell (Sam Hunt, Jelly Roll) booking a studio band at Nashville’s Sound Stage that seemed appropriate for a commercial country recording. The performance wasn’t over the top, but it was still too much; Smith and Crowell agreed they should lean on Trussell’s demo, so they repeatedly peeled back parts from the tracking session. Thus, Trussell plays numerous instruments amid the studio cats, and Alexander appears in some background vocal moments, though Whitters is the dominant female voice.

“This song was shockingly hard to do,” says Crowell. “It took a lot of different versions to get it to that [final] version.”

That’s also true of Whitters’ vocal. She hit the studio somewhere between two and five times — even she’s not certain how many sessions were involved. She sang the song in its entirety the first time around, but as the production morphed, they developed more specific ideas about how to use her voice. She was willing to keep coming back.

“I knew how special the song was to Conner,” she says. “I don’t think we knew at the time it was going to be a radio thing, but it meant a lot that he asked me to be on it, and I just wanted it to be right.”

In the final iteration, Whitters makes her first appearance singing harmony on the first chorus. She never sings as a solo lead until the final chorus, when her entry suggests that the female in the song is risking as much as the guy. “It definitely makes the payoff better if you kind of wait,” Crowell says. “It’s a little bit of a prize once you finally get the whole chorus from her.”

Valory released “Roulette on the Heart” to country radio via PlayMPE on April 8, providing some “Whiskey Lullaby”-like heft to Smith’s growing reputation.

“‘Creek’ is a really fun song that works great live,” Smith says. “But in the true heart of country music, what I want to stand for as an artist, I think this one begins to kind of unveil that.”