He may have had a checkered, hotel-room-trashing past, but Johnny Depp (also in the Cusack class) only gets cooler as he gets older. He owns a Caribbean island, for one, but he also seems to cultivate deep relationships that are meaningful. Sure, he’s close to his smoking-hot French girlfriend and his kids (who wouldn’t be?) but his friendships with icons and literary geniuses helped define him as somebody interesting and separated him from the worst of celebrity culture. He has beaches on his island named after gonzo journalist Hunter S. Thompson, and acting genius Marlon Brando. When Thompson committed suicide, Depp helped pay for the funeral, and, true to Hunter’s wishes, Depp built a huge cannon to shoot the author’s cremains out into the mountains of his Colorado home. That’s a professionally cool guy. As Thompson famously quipped, “When the going gets weird, the weird turn pro.”
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