Tony Bennett

Frank Sinatra once dubbed him the best pop singer in the biz, and when it's the Chairman of the Board himself doling out the praise, you're inclined not to disagree. Indeed, while best known by the masses for his signature song, "I Left My Heart in San Francisco," (recorded 45 years ago, no less), Bennett practically defies genre. Equally at ease in the company of jazz giants (his sessions with jazz pianist Bill Evans in the mid-'70s are the stuff of legend) and fawning pop stars who inexplicably and unexpectedly rechristened him a darling of the MTV crowd, he's definitely seen a resurgence in popularity among younger audiences in recent years. But does that make him a harbinger of hipness? One might argue that it wasn't Bennett who acquiesced to the new realities of rock and pop, but it's been more a move by those once rebellious rock stars (Elvis Costello and k.d. lang are prime examples) who peered back over their shoulders, reeling in admiration of the standards Bennett croons so convincingly. He's an artist who's well-ensconced in his 80s but is still as humble and tireless as ever. Ongoing accolades and a well-stocked mantle of Grammys and Emmys attest to his undiminished popularity and the fact that wherever he performs, his heart is left in his songs.