There's a long-running joke in Hollywood that one of the easiest ways to earn an Oscar is to either 'Ugly it up" or contract a disease. But, in recent years, one of the newer trends that can lead an actor to the podium is for them to take on a role where they play a person of same-sex orientation (a fact that has already become the stuff of satire). Over the past 10 years, plenty of actors have earned Oscars for playing gay roles, and the latest actor to join the club could be Matt Damon, who has signed to play Liberace's lover in Steven Soderbergh's biopic of the flamboyant musician.

So what's the big deal? Don't actors pretend to be different people all the time ... isn't that their job? Well, yes, but it's a little more complicated than that. Gay and lesbian political advocates have long lamented the sad state of affairs where straight actors are getting gay roles, instead of giving 'out' actors their chance to shine. So, while I question the idea that only gay actors could play a gay character, just as only straight actors can play straight characters, the sad fact is that Hollywood is still relatively puritanical when it comes to allowing their actors and actresses to be out and proud -- and that needs to change. But, that doesn't mean I think an actor (gay or straight) shouldn't play role any role they want ... just as long as they're good at it.

So on that note, I decided to give a little credit to five performances by straight actors in gay roles that transcended orientation and, ultimately, are just damn fine performances.

After the jump: my picks for the best of straight actors going gay for pay...

Sean Penn
as Harvey Milk in Milk

I have to tell you, what impressed me the most about Penn's portrayal of the trailblazing public servant (other than watching Penn romance James Franco) was how he managed to turn his usual dour self into the joyful and passionate public figure. Penn's portrayal of Milk earned him an Oscar (deservedly so) in 2008, and is a good example of how playing gay might be awards-bait -- but that doesn't mean it can't also just be one hell of a performance.

Guy Pearce as Felicia Jollygoodfellow in The Adventures of Priscilla, Queen of the Desert

I was about half-way through watching Memento when it dawned on me that this beautiful manly specimen dripping in tattoos was the same man who had reduced me to tears (both of the happy and sad variety) in the Australian classic, Priscilla, Queen of the Desert. Pearce's Felicia has my eternal respect because he brings to mind every tough-as-nails drag bunny I have met and admired over the years. Those ladies have the 'balls'' to be themselves, and no matter what the world might do to beat them down, they bounce right back looking fabulous (even with their jaw swollen shut).

Russell Crowe as Jeff Mitchell in The Sum of Us

Before Crowe arrived in Hollywood as the new tough guy in town, he used to do roles like Jeff Mitchell in The Sum of Us. Rarely do we ever get to see a father and son relationship that isn't fraught with tension over acceptance and understanding of his son's sexual orientation, but Geoff Burton and Kevin Dowling's Sum of Us subverts the usual tropes to create a romantic comedy where Jeff's dad is much more comfortable with his son's orientation than Jeff is.

Robert Downey Jr. as Tommy Larson in Home for The Holidays

Downey has played gay and bisexual characters before, but Tommy was probably his most well-adjusted (which is ironic considering the state he was in during filming of Jodie Foster's directorial debut). This tale of family awkwardness during the holidays captures just how hard it can be to be a part of a family, and Downey's portrayal grounds the film without a hint of flamboyance -- which is pretty impressive considering that 'flamboyant' is usually Hollywood's shorthand for gay.

John Leguizamo as Miss Chi-Chi Rodriguez in To Wong Foo, Thanks for Everything! Julie Newmar (in this clip, Leguizamo shares some on-set troubles with Patrick Swayze)

To be fair Leguizamo wasn't the first person to tackle this role, and it is awfully hard to top Mr. Pearce, but in the *US remake of Priscilla, dang, if Leguizamo's performance isn't the best thing about this flick. In a movie with plenty of cheap jokes to go around about guys in dresses, Leguizamo's Chi-Chi goes beyond cliché and becomes a real (if slightly flawed) person.

*Correction: Wong Foo was not an official remake of Priscilla, but at least I didn't call it a "shameless rip-off".