It's hard to be taken seriously as a musician when you're on People magazine's 50 Most Beautiful People list and your radio-friendly hits are habitually berated by the critics. That's the bane of Matchbox Twenty's 31-year-old pretty-boy frontman Rob Thomas, who's taken home enough platinum to fill a mine and scored solid hits on the Top 40, Alternative Rock, Adult Contemporary, Latin and Country Music charts. But rock and roll's most deceptively clean-cut pinup boy has hitched a long, dirty road from his Southern white trash roots to the top of the pops.

Rob was born Robert Kelly Thomas on Valentine's Day 1972 on a U.S. army base in Landstuhl, Germany. His parents divorced when he was two, and, for his formative years, he bounced between his young mother in a Columbia, South Carolina trailer park and his pot-dealing, moonshine-selling grandmother outside Myrtle Beach, Florida. By sixth grade, he and mom settled in a central Florida trailer park. As a wayward teen, Rob learned piano in order to seem sensitive and pick up girls at parties. He left home at 17 and went homeless for three years, occupying his days by hitchhiking and writing songs.

In 1996, after three years with the Orlando-based bar band Tabitha's Secret, Rob assembled Matchbox Twenty at the behest of Collective Soul producer Matt Serletic. Signed to Atlantic's Lava records, the band's first album Yourself or Someone Like You generated five bona fide radio smashes including the plaintive "3 A.M." and the controversial "Push" (which was misinterpreted by some as an anthem for batterers). The debut defied all expectations by going platinum 12 times over. Rolling Stone's critic griped, "There's too much complaint in Thomas's plaintiveness, and over an entire album his angst makes for a long day." The same year, Matchbox Twenty was named "Best New Band" in the Rolling Stone Readers Poll, defining the gulf between critical contempt and public embrace.

Thomas has written (or co-written) songs for Mick Jagger, Willie Nelson and Marc Anthony, but it was his 1999 collaboration with Carlos Santana on the aptly titled single "Smooth" that won him three Grammys and turned his generic moniker into a household name. Matchbox Twenty's sophomore disc Mad Season by Matchbox Twenty soon followed and went quadruple platinum, yet the critics still balked. Through it all, "sensitive" Rob cried all the way to the bank...and the altar. By '98, the once-pudgy saloon rocker dropped 30 pounds and made People's "Most Beautiful" list. In late 1999, Thomas married Marisol Maldonado, a gorgeous graduate student he met backstage in Montreal (and who stars in his "Smooth" music video). They live just outside New York and are planning a family.

Last year, Matchbox's third record, More Than You Think You Are, seemed to warm up the critics (if a three-star review in Rolling Stone is any barometer). With a live Matchbox Twenty EP in stores and a solo project on the horizon, Rob Thomas won't be pushed around any more. Recently, Playboy.com spoke at length with Thomas about surviving bad reviews, tripping at Disney World, getting high with Willie Nelson and much more.