49. Bruce Vilanch

These days, this comedy writer is basically a baller in the entertainment industry — he's won SIX Emmys and, as much as the Oscars suck, “Academy Awards Head Writer” looks pretty cool on your résumé. But his trademark chubby, schlubby look — offensive tee shirts, a few extra chins, hair that needs a good deep conditioning — worked only in the '90s: He was in the public eye then, but doing stand-up... so people were supposed to laugh at him anyway.