Louis C.K. once hit on Gwyneth Paltrow - it didn't go well
Like the time 20 years ago when C.K. hit on Gwyneth Paltrow at a party.
O'Brien and C.K. spent a lot of Thursday's show discussing the early days of O'Brien's tenure on NBC's "Late Night" -- he debuted as host of the NBC show on Sept. 13, 1993. C.K. was one of the first writers O'Brien hired.
The show's tenuous early days are well-chronicled. Less well-known is the story of C.K. hitting on Paltrow at the first "Late Night" Christmas party. It did not turn out as he planned -- hit play on the video above to find out why.
Want some more early-days-of-"Late Night" reminiscing? Watch this clip: