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13. Just DiCaprio And Clooney, No Big Deal

Leonardo DiCaprio was a classmate of Darlene’s in the episode “Home Ec” and George Clooney was a recurring cast member, before they made it big. Clooney had a few roles before he struck gold with medical drama ER. However, a role that stands out to many is the character “Booker,” Roseanne’s boss at Wellman Plastics. Roseanne obviously enjoyed working with Clooney and in her book Roseannearchy she describes him as being “the most fun person on earth to get drunk with” and shared that his practical jokes were “still legendary.”

George Clooney on Roseanne
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Leonardo DiCaprio on Roseanne
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