One of Chicago’s most funniest stars had already been a household name in the Black communities, but Friday was Bernie Mac’s first crossover step to the mainstream. After making millions laugh on HBO’s Def Comedy Jam, Mac played the lascivious Pastor Clever, who was looking to get a little “twenty-twin-twin” from Smokey for his cataracts. The role was in the vein of ones he’s done before, but his charisma and comedic timing couldn’t be denied. He followed up his time on Friday with work alongside The Wayans Brothers (Don’t Be a Menace To South Central), Spike Lee (Get On The Bus), and Brandy Norwood (Moesha). His work paid off as eventually he landed his own TV series (The Bernie Mac Show) and was starring in big box office movies like Ocean’s Eleven alongside Matt Damon and George Clooney. Unfortunately, on August 9, 2008, Mac passed away from sarcoidosis complicated by pneumonia.