A Video Compilation of David Letterman Flirting with his Female Celebrities

When it comes to flirting with guests, no one, and I mean no one could hold a candle to Family Feud’s Ray Dawson.  That guy was a total machine and made absolutely no bones about it.  But if I had to pick a distant second David Letterman would be at the top of my list.  Not only was Letterman one of the greatest late night hosts of all-time, he most certainly had a way with his female guests on the show.

My number one flirty relationship had to be he and Julia Roberts.   The two of them used to say things to each other where if my wife caught me saying those things to a female?  I’d be out the door.  Not to mention the fact these two kissed on the lips numerous times.   Anyway, in honor of Letterman’s skills with his ladies, there was a compilation clip put together earlier this year that I should have shared.  Well, now I’m sharing it.

These are clips of outrageous moments from Late Show with David Letterman involving female guest celebrities. Flirting, kissing, touching, leering, complimenting and saying inappropriate things. Courteney Cox, Julia Roberts, Uma Thurman, Demi Moore, Jennifer Aniston, Cher, Madonna, Gillian Anderson, Jessica Simpson, Gwen Stefani, Nicole Kidman, Charlize Theron, Paris Hilton, Catherine Zeta-Jones, Cameron Diaz, Emma Stone.



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