After stints as a weatherman, news anchor and stand-up comic, this sarcastic gap-toothed performer came to prominence in the 1980s with a late-night talk show on NBC. His offbeat signature bits (Tonight's Top 10, Stupid Pet Tricks), surly attitude and frequent send-ups of the entertainment industry made him a hit with critics and viewers. When NBC failed to give Letterman The Tonight Show after Johnny Carson retired, the disgruntled comedian jumped to CBS in 1993 and began hosting The Late Show With David Letterman. His long-term relationship with girlfriend and collaborator Merrill Markoe ended in 1987, and at age 56 he had a son with girlfriend Regina Lasko, whom he later married on March 19, 2009 (after dating her for 23 years). Letterman tries to be fanatically secretive about his private life, but this plan went off course in the wake of an extortion case in the fall of 2009, when he helped the Manhattan DA's office arrest a man who blackmailed him over information regarding his relationships with several female staffers. Off screen, Letterman is the co-owner of the Rahal Letterman Racing Team, which won the Indy 500 in 2004.