Josh Groban

In what was a glorious precursor to his current standing and legacy in the musical world, a 17-year-old Josh Groban served as a stand-in for the legendary Andrea Bocelli at the 1999 Grammy Awards, rehearsing his songs with another vocal demigod, Celine Dion. Of course, Groban has since elevated himself to (at the very least) equal status as Bocelli, selling 24 million records worldwide and producing four consecutive multi-platinum albums. Groban's signature single “You Raise Me Up,” a ballad sung with power and purity, proved he could sing, but recently he's set out to prove he has a sense of humor as well, by singing Kanye West tweets on “Jimmy Kimmel Live!” and by turning out an unexpectedly hilarious performance as Emma Stone's asshole boyfriend in Crazy, Stupid, Love.