Throwback Thursday: James Franco Pops Sean Penn's Gay Cherry

There are not many firsts in life. But in 2008, James Franco got to be part of Sean Penn's virginal experiences. The actor, 47-years-old at the time, had never kissed a man. Starring as Harvey Milk (Penn) and his younger gay lover Scott Smith (Franco), in the Gus Van Sant-directed Milk, both men knew they would eventually have to embrace.

In an interview with the film's screenwriter Dustin Lance Black for the November 2008 issue, Franco revealed that there were plenty of nerves on set, especially when it came to popping Penn's (gay) cherry.

James Franco: I think Sean and I had the first kiss of the film, and there were like 200 people watching on Castro Street. I was a little nervous. And it was a long kiss.

Dustin Lance Black: That was the three-minute kiss out in front of the entire population of Castro Street, not shut down. Everyone in the Castro came out to watch James Franco and Sean Penn make out.

Franco: Armistead Maupin came down to watch! [Laughing] So that was weird. It'd be weird kissing a girl in front of all those people. After the first kiss, it broke the ice. And then after our kiss Sean texted Madonna--his ex-wife, Madonna--and said, 'I just broke my cherry kissing a guy. I thought of you. I don't know why.' And then she wrote back and said, 'Congratulations.'

Black: You broke Sean Penn's gay cherry.

Franco: I did. I did.

While the nerves of the kiss may not seem that long ago, Franco has sense embraced men both on and off screen--he bumped bellies with Seth Rogen in a parody of Kanye West's music video for "Bound 2," snuggled under the blankets with Keegan Allen, and went deep inside the world of cruising for Interior. Leather Bar.

Now the actor can seen on stage--alongside Chris O'Dowd--in Of Mice and Men and on screen with Emma Roberts in the directorial debut by Gia Coppola, Palo Alto, which debuts in theaters on May 9.

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