Dierks Bentley used to boast of “living out every single guy’s fantasy,” touring 200 dates a year, tapping kegs at his concerts and coming home to a 42-ft. houseboat and a dog named Jake. These days Jake’s still around, but the man who titled his hit 2005 album Modern Day Drifter has left the houseboat behind and found himself another, more grown-up roommate: his wife of 15 months, Cassidy.
Curled up in the corner of a couch in their Nashville home, the country singer wraps his legs around his wife as Jake and George—another rescued dog—cuddle in their laps. A black-and-white photograph of the newlyweds shares wall space with a tender shot of Johnny Cash with June Carter Cash in his arms. “It used to be, when the tour bus pulled back in town, I’d try to convince the guys not to get off, because I didn’t have anywhere to go,” says Bentley, a medallion bearing the letter “C” dangling from his neck. “But now I’ve already got my bag packed and I’m ready to jump off. I love being here with her.”
With more than 150 dates to play this year on his first headlining tour and a newly released live concert DVD, Live and Loud at the Fillmore, to promote, the road still beckons. But home has a more permanent meaning for Bentley. “The boy’s got an anchor now,” says his friend Brett Beavers, who cowrote and produced all three of Bentley’s albums. “He had a little wild side to him, but now he’s got a root that goes down deep, and that’s Cassidy.”
The couple, both 31, first met in the eighth grade, at Phoenix’s Ingleside Middle School. “I had a crush on her the whole time, but I wasn’t cool enough,” says Bentley, who recently traded his self-described Greatest American Hero curls for a shorter, hipper cut. “I was way too immature and into drinking beer and guns and blowing things up.” As Cassidy sums up, “He was just trouble.”
Eventually, after each went out with the other’s best friend, they tried dating in high school. But then Bentley moved to Nashville at 19 and scored honky-tonk gigs, while Cassidy took a job in a San Francisco advertising firm. During an on-again, off-again long-distance relationship, “I used to write her all these crazy love letters that I’d FedExed out to her,” says Bentley, adding with a laugh, “That’s why I married her! I was worried I’d get blackmailed with those letters!” Cassidy jokes back, “I did save them and thought I could always sell them on eBay!”
As his success grew and he began touring with Kenny Chesney, Bentley nearly gave up on his longtime crush: “I just didn’t think I could make her happy because my life was so crazy.” Until, that is, Feb. 4, 2005, when she came to see his show in Las Vegas. “When she walked on the bus, I just knew,” he says. Adds Cassidy: “It was a weird feeling, and it was right when I saw him … I cried when I said goodbye.”
Bentley soon traded in houseboat life for a 3-story, 2,100-sq.-ft. contemporary home in Hillsboro Village, and Cassidy quit her job in San Francisco and moved in. (She is now freelancing in advertising and working on a documentary film.) Ten months later, during a tour date in Las Vegas, Bentley surprised her with a proposal. The morning after, he surprised her again with a plan to elope to Mexico the very next day; he’d even had a stylist friend bring a dress for her. “I was nervous,” he says. “You don’t want to pick out a woman’s wedding dress!”
“I was speechless—I had just gotten engaged the night before,” says Cassidy. “We got married in a little chapel in Mexico, and it was beautiful and private and real.” (The Chloé dress that was selected for her, she adds, “was perfect.”)
On days when Bentley is home from touring, the couple settle into a domestic routine. They walk the dogs to a local café, Fido’s, for morning coffee, and afternoons are often spent riding his Harley on country roads (Dierks drives; “He’s the worst backseat driver,” says his wife. “It’s chronic!”) or exploring the 40 acres they recently bought south of the city, where they plan to build a new home.
On tour, though, “you get on the bus, and you turn into a 13-year-old again,” says Bentley. “You play video games and tell the same jokes over and over again with the guys, and I love that.” Still, some things have changed. He has widened his bunk on the bus he shares with his four bandmates to accommodate Cassidy when she joins him twice a month. And, he says, if the future brings little Bentleys, they might just splurge for their own private bus. Cassidy laughs at the thought: “Then it would be me and the babies on our bus, and he’ll be with the band!” Dierks’s eyes light up. “We could turn my bunk into a pub,” he jokes. “When you marry, yes, you move into a different role, but I’m still a little kid onstage living out his dream.”