Leonardo DiCaprio has been played on 11 lists, including 5 lists in The 1999 Lee Atwater Invitational Dead Pool.

 List User Stiffs Points 
1.Dr. Jack Fanclub 3Chachi11
2.ByzantiumByzantium00
3.Flash & Scoop's Hate ListUSER0049800
4.KingV 3USER0053000
5.The Funky UndertakersUSER0029400
 

 

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Winning an Academy Award probably paled in comparison to starring in 1981's "The Harlem Globetrotters on Gilligan's Island"

(d) July 15th, 2017