Expressing a desire to show his “serious side,” and with Conan’s permission, Farley steps over to an isolated stage and grabs a microphone, crooning out a ballad about his life as a sad, fat, funny man. Receiving his laughter and applause, he then goes to exit, only to get trapped in the curtain, inevitably bringing the whole thing crashing down on his head.


Obviously, Farley and O’Brien intended this little metaphorical parable as a comedy bit, and it is, indeed, very funny, because Chris Farley was a very funny guy. But it wouldn’t be as funny if he wasn’t simultaneously conveying the sense that all the jokes he’s singing about his weight and his unhappiness are actually pretty true, a bolt of honesty that became much harder to look past in the wake of his death just a few years later. Farley himself would probably have rolled his eyes at the idea that this was a “cry for help”—he seems as interested in mocking the tradition of the sad clown as he is in acknowledging his place in the archetype—but that doesn’t stop it from being surprisingly painful to watch, even 20 years on.