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John Locke as Russell Simmons
Baldies aside, Locke and Simmons have several things in common. They're both very spiritual and well known for their calm personalities. Oh, and yes I know Russell Simmons isn't a rapper but he's a key figure in Hip Hop and the parallels between him and Locke just had to be mentioned.
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Shannon as Nicki Minaj
If there's anyone on the island who would even think of referring to another woman as "Barbie" or calling things "fetch" it would definitely be Shannon.
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Jack as Jay-Z
When it comes to leadership, both Jack and Jay-Z certainly come to mind. Although one has succeeded at his leadership roles and the others leadership skills are somewhat debatable.
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Sawyer as 50 Cent
Aside from looking good shirtless, both 50 Cent and Sawyer reign supreme when it comes talking shit and of course instigation.