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While he may not have gone into details about why he left Chappelle’s Show back in 2006 (he’d already discussed that on Letterman), one topic Dave Chappelle did talk about on his appearance on The Tonight Show was the incredible time he first met Kanye West—and even back then it seems Kanye had the attitude of a wannabe-bigger-than-Jesus mega-ego.

After discussing when he first met The Roots at a shopping mall in Portland (“They thought I was a lost Root”), he then goes on to chat about his first encounter with Kanye. It was back in 2003 before West was famous and involved West coming to see some previously unseen Chapelle sketches—and it has an amazing moment of Kanye self-worth that, with hindsight, was a foreboding warning of the egomania to come.

Check it out in the video above and then feel depressed because you’ll never have a story as cool as that to tell.

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