He has played a hardened ex-convict, a mentally challenged man and a California stoner. But Sean Penn's current portrayal of a gay politician has some critics calling it his best performance ever.
How this tough-guy, straight actor was able to step into the shoes of Harvey Milk, the country's first openly gay politician, in the new film "Milk" is as much a testament to Penn's talent as it is to a culture that has become more accepting of gays.
Yet, while Penn receives raves for his performance, some in the gay community wonder aloud why a gay actor could not have played his role or any one of the others cast with straight actors James Franco, Emile Hirsch and Diego Luna.
"It has almost become a rite of passage for these leading Hollywood actors to take on a gay role," said David Hauslaib, editorial director of the gay and lesbian Web site Queerty.com. "I think Sean Penn's career can only benefit from a role like this. The same was true for Heath Ledger and Jake Gyllenhaal [who played gay lovers in 'Brokeback Mountain']."
"I think there's probably less fear of being typecast the way that actors in the last century had fears," said New York casting director Tiffany Little Canfield. "It's not as big of a risk. I've never heard in all my casting of an actor being concerned about playing a homosexual character."
A cultural shift that turned "Will and Grace" into a Top 10 sitcom and 2005 gay romance "Brokeback Mountain" into a mainstream success has also made the American audience more open to gay characters.
But some charge Hollywood has warmed to gay characters but not to gay actors.
"When straight men get these parts, the gay community feels slighted," Hauslaib said. "A whole number of roles could have gone to openly gay actors to give them visibility. Instead they went to well-known straight actors. It's just another notch in a belt for a straight actor. For a gay actor it could have been a breakout role."
Problem is, even in liberal Hollywood, there remains a dearth of openly gay A-list actors who can open a film.
"It was hard to find gay actors who were out," the film's openly gay director Gus Van Sant told Reuters. "There really aren't [many]. You could do it, but they would be unknowns and that would be fine with me, but the money [financiers] would start to get nervous."
After a dozen years of trying to get "Milk" made, the film finally received the green light when Penn signed on.
"Of all the colors in the rainbow, green [the color of money] still seems to be the most important," Canfield said.
She points out that the number of A-list movie stars who can get a movie produced just by signing on is already small. For gay actors, it's nonexistent. Prominent openly gay actors Sir Ian McKellen and Rupert Everett haven't been able to do it, Canfield said.
"Who are our big movie stars who are openly gay? Is there an A-list?" Canfield said. "No, there is not."
Meanwhile, audiences appear to have little trouble accepting tough guy Penn as a gay man on screen -- in his personal life, he has scrapped with paparazzi and carried a rifle through New Orleans after Hurricane Katrina.
"I think he does a remarkable job," said Gregg Kilday, the film editor for The Hollywood Reporter. "He seems to inhabit Milk's milieu, his mannerisms and his spirit."