David Letterman

We don't know what shocks us more:

David Letterman's bizarre on-air confession-turned comedy routine?

Or that it was an Emmy-award winning producer of the CBS news magazine 48 Hours who was arrested and charged with attempted grand larceny for allegedly attempting to use Letterman's now-acknowledged sexual relationships with staff members to extort $2 million from him?

Madonna told David Letterman last night that she will won't be marrying for a third time.

"I think I'd rather be run over by a train," she said. Madge also, evidently, has never had a slice of New York pizza (how is this possible?), so Letterman took her up the street to grab a slice. She doesn't eat cheese (of course), so she took hers with basil and olives on top.

We don't know many New Yorkers who would say that's the same!

And the number one thing to do when you're a 61-year-old misanthropic talk show host?

Marry your baby mama.

David Letterman announced to his audience on Monday that he married his longtime girlfriend and former assistant, Regina Lasko, 48, before a Teton County justice of the peace on March 19th in Choteau, Montana.

Their 5-year-old son Harry was one of the witnesses.

Last night, the Emmys celebrated their sixtieth anniversary with the least funny, most awkward award show opening in history. You know David Letterman was sitting on his Barcalounger thinking, “No one will ever be able to give me grief from the ‘Oprah-Uma’ gag ever again.”

Will Smith knows how to kiss-up to talk show hosts. Literally.  

When the Fresh Prince sat down with David Letterman to promote his new summer blockbuster Hancock, things got…intimate.

As Smith arrived on stage Letterman said, "You look great - every time I see you, you just look better and better." Smith responded by planting a wet one on the host and joking, "Dave, once you go black you never go black."

It looks like Will and Dave shared a tender moment. Awwww. They should get married in California.