But with a new album, a new single and a new record deal, Vassar is making his play for country's A-list.
"In our career and business I think change is really good. Sometimes you can get complacent, whether it's with band members or managers or whatever. Sometimes you just need a fresh start," says Vassar, a muscular guy of 43 with blond hair and blue eyes.
The album is his first on Universal South Records after a decade with Arista Records. He switched labels last year in an attempt to shake things up.
At Arista, Vassar was in a deep pool with labelmates Carrie Underwood, Alan Jackson, Brooks & Dunn and Brad Paisley. With that lineup, it's easy to get lost.
"In today's world there are so many things out there for people to get distracted by. It's hard to break through the clutter. You really have to have a focused, huge push," said Lon Helton, editor and publisher of the trade publication "Country Aircheck." "Perhaps in this case a new label will be able to do that for Phil. I'm not taking shots at the old one, but you can see how when you're in a group of superstars, that's where their attention naturally gets focused."
Not that Vassar was off country music's radar. Beginning with his 2000 self-titled debut album, he's racked up two No. 1 hits ("Another Day in Paradise" and "In a Real Love") and several other Top 10s including "Carlene," "American Child" and "Last Day of My Life."
But he's yet to break into country's upper echelon, alongside the superstars like Tim McGraw and Alan Jackson who've recorded his songs.
"I think the key for Phil is touring," said Fletcher Foster, senior vice president/general manager of Universal South, whose roster also includes Joe Nichols, Shooter Jennings and Cross Canadian Ragweed. "When people see him perform they realize he's an entertainer. ... I think he's one of those artists who hasn't seen his star potential yet."
While Vassar, a divorced father of two young daughters, says he prefers the relative anonymity that allows him to be a "normal person," he's also keen to reach another level a big reason for the label change. He admires the career trajectory of musical heroes like Bruce Springsteen and Willie Nelson, who built a steady, loyal following before they became superstars.
"I never wanted to have a meteoric beginning because where do you go from there? I always wanted to have a career."
Vassar grew up in Lynchburg, Va., where his father worked in a factory and sang in clubs on the weekends. At one point, his dad, who is now deceased, owned a restaurant where he performed and the younger Vassar bussed tables.
As a high school freshman he taught himself to play music on a borrowed piano, between two-a-day football practices. He didn't own one until after he moved to Nashville in 1987.
At first, Music Row didn't know what to make of Vassar. He didn't wear a cowboy hat or sing with a twang, and he played piano instead of guitar.
"They'd say 'Nobody cares about piano players. You've got to have a hat on and a guitar.' I'd say, 'This is my instrument take it or leave it.' And so they left it."
By 1995 he'd saved enough money to buy a restaurant and club where he'd been performing. Everyone from motorcycle gangs to Music Row executives would drop by for the Italian food and the live music.
"It was packed all the time. It was like 'Cheers' with a band," Vassar recalled.
One of the patrons whose father turned out to be 1960s and '70s pop singer Engelbert Humperdink asked him for a demo tape of his songs, and Humperdink ended up recording "Every Once in a While," a song Vassar wrote with one of his bartenders.
He signed a publishing deal and pretty soon was writing hits for Jackson ("Right on the Money"), McGraw ("My Next Thirty Years"), Colin Raye ("Little Red Rodeo"), and Jo Dee Messina ("Bye, Bye").
The record labels couldn't ignore him anymore and Arista finally signed him in 1998.
"I'm lucky to be here after five records," he says, "I feel really, really blessed."
As for the restaurant, Vassar sold it after his first solo hit, "Carlene."
"My dad always told me 'Don't get in the restaurant business and don't get in the music business,' he shrugged, "and I went and did both."
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