Welcome to iPlayboy 1953-2020Official Playboy Archive

Spring 2020

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20Q |

Kevin Connolly Ashley Jude Collie

Entourage's savvy wingman lives the ultimate Hollywood life. Who else hangs with Leonardo DiCaprio and Tobey Maguire, dated Nicky Hilton and directed Robert Downey Jr.? It sounds like a certain TV show, doesn't it?

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