10. Rick James – Chappelle’s Show
We all miss Chappelle’s Show, Dave Chappelle’s infamously abbreviated sketch comedy show from the mid-aughts. Of course, we all remember when Chappelle portrayed Rick James in Charlie Murphy’s True Hollywood Stories, a skit centered on Charlie Murphy’s early days in Los Angeles with his brother Eddie. The segment spawned a catchphrase that Chappelle hates to this day, but the fact that fans shout it at him more than 10 years later only confirms how unassailable this sketch remains.