When Ryan Phillippe lifts up his shirt in the middle of the bar at SoHo’s Crosby Street Hotel, it’s surprising that no one faints. He is, after all, a movie star—with taut muscles, smooth, caramel-colored skin, and a chiseled, ready-for-my-close-up mug. To think that someone might walk by, catch a glimpse, and collapse in excitement is not out of the question. Surely it’s happened before. But not today. Today everyone remains calm.
To be fair, it isn’t as tawdry as it sounds. Ryan has lifted his shirt simply to show off his tattoo—an image of his son Deacon’s hand gripping Ryan’s grandfather’s hand—from the beloved artist Mister Cartoon. Like his career, Ryan takes his tattoos very seriously. “It’s really beautiful and soulful,” the 35-year-old actor says. “I went in there with this idea, and Cartoon loved it. He’s a soulful guy, and I have a connection with him that’s personal. I was so excited because he’s the top hip-hop artist, and I’m such a hip-hop head. He’s literally done everybody … Kanye West, Xzibit. You go into his studio and there’s a picture of him tattooing Eminem’s skull. It’s sort of like a brotherhood. Cartoon said, ‘You’re part of the family now.’ It’s a cool family to be a part of. He’s done three on me now.”
For most people, Cartoon’s waiting list is months long, but it helps if you’re a famous actor who’s appeared in more than 20 movies, including Flags of Our Fathers, Crash, 54, Cruel Intentions, and this month’s MacGruber, a big-budget comedy based on Saturday Night Live’s popular MacGyver spoof.
Ryan’s show business beginnings are the stuff of Hollywood legend: He was discovered as a teen while getting a haircut in a Delaware barbershop. Soon after, he was starring in the soap opera One Life to Live, as the first gay teen ever to appear on daytime television. It was a risky career move—one of many ballsy chances he would take over the next two decades. “I was shunned by the church after I did it,” Ryan recalls. “Ostracized, in a way. It was a nerve-racking job at 17, when you’re just kind of understanding your sexuality. I didn’t know any gay people. I was nervous and insecure. The other actors were like, ‘You’ve got to speak up.’ But it was an amazing learning experience. It grew me up.”
At 19, while on location in England for his first big movie, White Squall, Ryan had another coming-of-age moment: He got his first tattoo. He takes a sip of his tequila cocktail and points to a Japanese character that stands for spirit or soul on his right arm.