July 10, 2005 - Kevin Winter/Getty Images Entertainment more pics like this »
Britney Spears

Britney Spears confirmed her first pregnancy on her website, but in May 2006 she kicked it up a notch, revealing her second pregnancy on the Late Show and joking, "Don't worry Dave, it's not yours." Letterman cracked, "Oh. Well, I think that's good news for both of us."