Prince

Prince
On February 4, 2007, Prince performed at the Super Bowl XLI halftime show in Miami, Florida, despite the fact that his music and appearance are the complete opposite of what most football fans are into.

Neil Patrick Harris

Neil Patrick Harris
Neil Patrick Harris played a teenage doctor in the family TV series Doogie Howser, M.D. On November 2, 2006, People published a statement from Harris in which he revealed his homosexuality to the public. He currently stars in the very funny sitcom How I Met Your Mother.

Andy Richter

Andy Richter
After serving as Conan O’Brien’s comedy sidekick for seven years, Andy Richter decided to leave Late Night with Conan O’Brien in 2000. Since then, he has starred in the TV shows Andy Richter Controls the Universe, Quintuplets, and Andy Barker P.I. and has played bit parts in various sitcoms and movies. Clearly, he made the right choice.

Update 2/15/11: In June 2009, Andy Richter went back to being Conan O’Brien’s sidekick, first on The Tonight Show with Conan O’Brien and now on the TBS late-night talk show Conan.

Leonard Nimoy

Leonard Nimoy
In 1967, Leonard Nimoy debuted his song “The Ballad of Bilbo Baggins” on the TV show Malibu U. A year later, the song was included on his album The Two Sides of Leonard Nimoy, which also featured his versions of “If I Was A Carpenter ” and “Gentle on My Mind.”

“The Ballad of Bilbo Baggins” music video: