Louis C.K. once hit on Gwyneth Paltrow - it didn't go well

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Louis C.K. was the sole guest on "Conan" Thursday night (Sept. 19), and as such he and Conan O'Brien had a lot to talk about beyond the usual "what you're up to now" kind of talk-show banter.

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:

Photo/Video credit: TBS