Do you remember this drunk(?) Letterman guest?

http://www.youtube.com/watch?v=ALapHYNSmoA Here it is. He was ripped.

Peter O’Toole was on Letterman once and seemed to be completely out of it. At one point while talking to Dave, he casually pulled out a cigarette and started smoking it. Dave’s eyes nearly exploded out of his head.

I remember Captain Beefheart (Don Van Vliet) making an appearance on Letterman completely off his ass, drinking out of a bottle in a brown paper bag throughout.

This was back when Late Night was one of the few things worth watching on network television, and long before any trace of mediocrity had begun to creep in. Around 1985, maybe?

At work, so no Youtube search, sorry.

Crispin was a good friend of mine from the ages of 14 to 18. We lost touch when I went away to college and his acting career started to take off. We hadn’t spoken in over five years when that clip aired but I am nearly certain, knowing what I know about him, that he was doing a character while stone cold sober.

Oliver Reed was the first one I thought of. Not only drunk and incoherent but fairly belligerent also, IIRC. I don’t remember the sailboats though.

The best part about this was when she came back on a couple years later. They had an intro to the show with Dave and Paul chatting in the hallway.

Paul: Who’s on the show tonight, Dave?

Dave: Well, we’ve got Dan Patrick from ESPN, and Farrah Fawcett.

Paul: Dan Patrick! Oh man! Remember last time he was on the show? Jeez, what was he on?

Dave: Hee hee, I don’t know!

Both of them share a good laugh for several seconds.

Paul: So, who else did you say was on?

Dave: Uh, Farrah Fawcett.

Paul: Has she been on before?

It was Oliver Reed:

This is perhaps his most infamous TV appearance, though.

WOOHOO! I WIN! Where’s my prize?? :smiley:

I think most people (seeing the show) did not get the impression Glover was drunk or high, simply that he was a mentally unstable person.

From Wiki

[edit] Late Night Appearance

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I actually remember seeing that show when it was broadcast. Spooo-fucking-keeee. Have a look at the clip. The guy is obviously high on something.

He would do characters like that all the time when I knew him. He’s playing a part, not that different from his part on The River’s Edge or one of his characters in a David Lynch film. As astro’s link shows, it was a specific character that he used in a later film. It was a put on, I assure you.

Although Oliver Reed is not in this list, there’s still plenty of awkwardness go to around:

Cracked.com–Letterman’s 9 most hilariously awkward moments