Ryan Cabrera

It’s difficult to muster too much pity for someone so undeservingly privileged, but Ryan Cabrera, who plays the Rave tonight at 8 p.m., is becoming one of pop music’s most pathetic figures. Mentored by manager Joe Simpson, who signed the pretty-boy singer because of his highly publicized (and, thanks to MTV, televised) relationship with daughter Ashlee Simpson, Cabrera never became a bona fide star despite the considerable financial backing. Pouring further salt in his wounded pride, Ashlee Simpson went on to marry a far more successful dudeFall Out Boy’s Pete Wentzleaving Cabrera something of a third-rate K-Fed. Cabrera recently shed his once-trademark bleach-blond, Abercrombie & Fitch hair spikes in favor of a shaggy-haired, homeless-rocker-confident-in-his-sexuality look, but the reinvention did nothing to revive his career. His most recent album of new wave-inspired commercial pop, The Moon Under Water, debuted pathetically at the tail end of the Billboard 200 (No. 177) before falling off the charts completely just one week later.