Straight Actors Who Have Played Gay Characters In Movies

These actors excelled at playing gay characters in these movies.
Harriet King May 3rd 2018 Entertainment
There's something of a debate going on in Hollywood at the moment about who gets to play which roles. Bryan Cranston has taken a role as a disabled man in 'The Upside,' which has drawn criticism from some quarters. There are plenty of real-life disabled actors who wanted that part.
Similar conversations have taken place about straight actors playing gay roles, or transgender parts going to actors who aren't actually trans. Trans actors feel that it's hard enough for them to get major parts without suitable roles being taken by people who aren't really trans. It's become a controversial issue.
For filmmakers though, it's a question of giving the roles to the people who can play them most convincingly, regardless of their ability or disability, race, orientation or gender. There are plenty of straight actors who have excelled playing gay characters on screen. Here are just a few of them!
1. Tom Hanks - Philadelphia
Tom Hanks has to be considered as one of the best character actors of his - or any - generation. The versatile performer has delivered world-class performances in almost every role he's ever been given, committing himself entirely to his performance and earning plenty of acclaim in the process.
One of the best examples of that would be in the part of Andrew Beckett in the seminal movie 'Philadelphia' in 1993. The impactful film was loosely based on the true story of lawyer Geoffrey Bowers, a lawyer with AIDS who was fired from his job and went on to sue for wrongful dismissal and discrimination. It's one of Hanks' all-time best performances, and one which won him an Oscar, so nobody could deny that he was the best choice for the job. In real life, Hanks has been married to Rita Wilson since the late 1980s.
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2. Matt Damon - Behind The Candelabra
There were two well-known straight men playing gay characters in the 2013 film 'Behind the Candelabra', which prompted an outcry in some reaches of the Hollywood gay community. By 2013 there was far less stigma attached to being gay than there was in the 90s, and there are plenty of openly gay characters who could have appeared in the lead roles of the Liberace biopic. Despite that, the producers went with Matt Damon and Michael Douglas.
Whatever the reasoning, it was an inspired choice. Douglas was excellent, but the film wouldn't have been the same without the incredible performance of Damon in his supporting role as Scott Thorson, Liberace's assistant and lover. The chemistry between the two was electric and made a success of the film despite the fact that Damon, married to his wife Luciana since 2005, is straight.
3. Jim Carrey - I Love You Phillip Morris
This film was a break with tradition in a number of ways for comic actor Jim Carrey. The star of 'Ace Ventura,' 'The Mask' and 'Liar Liar' was known as a gifted and funny performer, but he wasn't an obvious choice for gritter roles. There are funny moments in 'I Love You Phillip Morris', but it's a black comedy with many darker moments.
The studio took a risk by casting Carrey in the lead as gay con artist Steven Russell, but it was a risk that paid off. Carrey showed unexpected depth and charm in the part, which opened the door for him to expand his acting repertoire. In real life, the Canadian has been in relationships with many famous women including Renee Zellweger and Jenny McCarthy. In the movie, he's so convincing that you'd never doubt that he was attracted to men if you had no prior knowledge of him.
4. Michael Douglas - Behind The Candelabra
Having discussed Matt Damon's performance in this film, we were inevitably going to return and talk about Michael Douglas, too! Douglas has made a whole career out of playing tough alpha males; sometimes vicious ones. This is the same man who played Gordon Gecko in 'Wall Street,' but here is displaying his incredible range as an actor.
In some respects, the casting made perfect sense. Liberace always pretended to the world that he was straight, and so casting a straight actor helped to portray the underlying conflict within his character. Douglas completely disappeared into the part, giving a performance worlds away from the many roles he's played in which 'getting the girl' was part and parcel of the script. You could almost have forgotten that he's been in one of Hollywood's most famous marriages with Catherine Zeta-Jones for nearly twenty years.
5. Jake Gyllenhaal - Brokeback Mountain
Jake Gyllenhaal has been known to date some of entertainment's biggest female stars, including Reese Witherspoon, Kirsten Dunst, and Taylor Swift, but he's better known for his part in 'Brokeback Mountain' than anything else he's ever done in his life or career. He already had a great reputation in the movie world before this film, but the part hugely enhanced his status.
The relationship on screen between himself and Heath Ledger was utterly captivating and convincing. Gyllenhaal became conflicted rancher Jack Twist before our eyes and showed us every flickering second of his character's doubts and torments. The bond between the two men grew so strong in real life that Gyllenhaal went on to become the real-life godfather to Ledger's daughter! The ole won Gyllenhaal an Oscar nomination, and many believe he should have gone home with the award.
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6. Charlize Theron - Monster
Charlize Theron goes so deep into her role as Aileen Wuornos in the 2003 film 'Monster' that she's almost unrecognizable. In real life at the time she was dating Stuart Townsend, but she had no difficulty convincing the world she was a lesbian in the movie. Her dedication to the part is absolute, and it's no surprise that it won her an Oscar.
In 'Monster' Theron's character is a mentally-broken prostitute who snaps and goes on a murderous rampage. Stripped of her makeup, bathed in sweat and wearing a permanently unhinged expression, Theron completely transforms into her part in a way that surprised and delighted critics. The film is a biopic, and thanks to Theron's acting abilities, the resemblance between her and the real-life Wuornos is striking. It's a tragic tale with a tragic ending, but it's an incredible movie.
7. Heath Ledger - Brokeback Mountain
Much like 'Behind the Candelabra,' 'Brokeback Mountain' was a film about gay relationships that featured two straight men in the lead roles. We already know about Jake Gyllenhaal, but Heath Ledger's casting as Ennis Del Mar was perhaps an even bigger risk for the producers. Back in 2003, Ledger was known more for his good looks and his appeal to teenage girls than he was for his abilities in grittier parts, but the performance he gave was a revelation.
Everybody knows what happened to Ledger next; he went on to give a definitive performance as the Joker in 'The Dark Knight' before his life was tragically cut short. 'Brokeback Mountain' may be the movie we should remember him for best, as it defined his career and brought him an Oscar nomination. Ledger is survived by a daughter who'd never have been born had he not taken this part; the mother is Michelle Williams, who he met while making the movie.
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8. Jared Leto - Dallas Buyer's Club
Jared Leto is a man who seems to polarize audiences. He got a lot of criticism for his own interpretation of the Joker character in 'Suicide Squad' (with his performance being compared unfavorably with Heath Ledger's interpretation of the same role), and his band Thirty Seconds to Mars have been bottled off stage at music festivals, despite a string of hit songs. He did manage to unite the audience of the 2013 movie 'Dallas Buyer's Club' though.
Leto completely transformed himself to play the part of Rayon in the movie and was utterly compelling and convincing as a transvestite dealing with AIDS. Leto, like lead actor Matthew McConaughey, dropped a considerable amount of weight for the part in order to make things realistic. It was that kind of dedication that saw him nominated for an Oscar. In reality, Leto is straight, and was briefly engaged to Hollywood superstar Cameron Diaz.
9. Ewan McGregor - I Love You Phillip Morris
It wasn't just Jim Carrey playing outside of his own sexuality in 'I Love You Phillip Morris'; 'Star Wars' and 'Trainspotting' star Ewan McGregor was joining in on the action too. The black comedy actually featured McGregor in a number of roles due to its unusual plot, but the most significant of them was the title role of Phillip Morris himself.
McGregor had to get into the mind and persona of not just one gay man but several, as a number of his other parts in the film were as gay and bisexual characters. Despite being married to wife Eve since the mid-1990s, McGregor seemed to take to the parts swimmingly, managing to imbue each of the different parts with its own personality and never appearing to be less than convincing in any of them. It's just one more example of McGregor's gifts as a character actor; we're yet to see him come across a role he can't make his own.
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10. Sean Penn - Milk
For a long time, Sean Penn's successful Hollywood career was overshadowed by the fact that he was better known to the press as 'Mr. Madonna', having been married to the pop megastar for the second half of the 1980s. After that, he was married to Robin Wright, best known for her portrayal of Claire Underwood in 'House of Cards.' Perception of him changed after his incredible and moving role in 'Milk' in 2008.
'Milk' is a biopic of Harvey Milk, the real-life politician who became the first openly gay man to be elected to office in California during the 1970s. It's a powerful and unique film, and a fitting tribute to a unique and inspiring man; a man whom Penn brought to life on screen with skill and sincerity. It serves not only as an excellent drama, but a candid insight into what life was like for gay people in the San Francisco of the time. Unsurprisingly, it brought Penn an Oscar.
11. Philip Seymour Hoffman - Capote
Philip Seymour Hoffman played a number of gay or bisexual roles over the course of his career, to the point where people who weren't familiar with his personal life actually thought he was gay. In reality, he was in a committed relationship with Mimi O'Donnell from 1999 all the way through to his tragic death in 2014.
Of all the gay roles that Hoffman played, the one he received the most attention and credit for was 'Capote,' the Truman Capote biopic which hit cinemas in 2005 and won him an Oscar. The movie captures Capote at a pivotal moment in his life, drawn into a grim fascination with the murders of Perry Smith. He turns Smith's story into the book 'In Cold Blood' but is traumatized by Smith's execution and never writes again. Hoffman's performance captures Capote's sorrow and torment perfectly.
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12. James Franco - Howl
James Franco is another actor who's made the portrayal of gay and bisexual characters something of a hallmark for himself, despite being heterosexual to the best of our knowledge. He's been in public relationships with fellow performers Ahna O'Reilly and Marla Sokoloff to name just two.
In 'Howl,' Franco is incredible as the poet Allen Ginsberg. 'Howl' is also the title of Ginsberg's most famous work; an epic poem which serves as both a lament at the state of the society in which Ginsberg lived, and the discrimination that gay men faced simply for being gay. Ginsberg was openly gay during a time when nobody was and suffered a great deal for his honesty about the subject. He even had to suffer the indignity of going to court to prove that 'Howl' wasn't obscene, with the judge eventually ruling in his favor.
13. Bradley Cooper - Valentine's Day
Bradley Cooper is one of the most popular pin-up stars, with posters and pictures adorning the bedroom walls of many teenage girls, so it will be a relief to them to find out that he isn't gay in real life! He's actually dated Zoe Saldana and Renee Zellweger, but that didn't prevent him from capturing our hearts with his portrayal of the gay character Holden in 2010's 'Valentine's Day.'
The film wasn't an unqualified success; the huge ensemble cast felt like quantity over quality, and critics weren't impressed by it. Despite that, it performed well at the box office and was received warmly by the paying public. Holden and his partner Sean are the only gay characters in the film, which given the size of the cast felt like under-representation in 2010. The critical failure meant that Cooper's search for his first Oscar continues.
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14. Naomi Watts - Mulholland Drive
Mulholland Drive is a movie that's more complicated than it initially appears to be and was a labor-heavy job for star Naomi Watts, who played two different characters in the film. The one that gained her entry to this list was struggling actress Betty Elms, who doesn't see herself as gay but nevertheless finds herself falling in love with a woman with a mysterious past. As the character wasn't gay when the film began, casting a heterosexual woman into the part may have made more sense here than it did with other movies we've discussed.
Watts has been with actor Liev Schreiber for fifteen years in real life. The other character she plays in the film, Diane, may also be gay; although this is never explicitly confirmed on screen. True to the style of director David Lynch, much of what happens in the film is open to interpretation, with no right or wrong answers.
15. Meryl Streep - The Hours
Meryl Streep is one of Hollywood's finest actresses, making fantastic films for longer than most of us have been alive. She's displayed a tremendous amount of variety during her career, so it's not surprising to us that she's taken on a prominent lesbian role within her body of work. She really caught the eye of cinema-goers and critics in 'The Hours' in 2003, in which she played lead character Clarissa Vaughan, picking up plenty of awards along the way.
In real life Streep has been married for much longer than most Hollywood stars manage, having tied the knot with husband Don Gummer back in 1978, but that didn't stop her giving a commanding and convincing performance in the film, which is a big-screen adaptation of Michael Cunningham's 1998 book. The Hours is one of the few works of fiction that's won awards as both a movie and a novel; the original text won Cunningham the Pulitzer Prize.
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16. Robert de Niro - Stardust
You could split Robert De Niro's career into two halves, and how you perceive him will depend on your age. In the earlier part of his career, he was the Alpha-male tough guy star of 'Taxi Driver,' 'Raging Bull' and 'Goodfellas,' as well as the second 'Godfather' movie. To a younger audience, he's more recognizable as the cranky dad from 'Meet the Fockers.'
Between all the macho-man parts and the comedy though, he's found time to give a convincing and sensitive depiction of a gay man in 2007's 'Stardust' in which he played Captain Shakespeare. De Niro has been married to Grace Hightower since the 1990s, but in 'Stardust' he managed to see off the more obvious choice of British actor Stephen Fry for the part. Jack Nicholson was also under consideration at one point, but de Niro seemed right at home in the fantasy adventure.
17. Robert Pattinson - Little Ashes
Taking this role was an intelligent move on the part of Robert Pattinson. He'd been cast in the 'Twilight' movies and was aware that he'd earn a lot of money from them, but also ran the risk of being typecast. To demonstrate that there was a lot more to his acting skill than portraying a slightly emo vampire, he also accepted the part of Salvador Dali in 'Little Ashes,' which was released the same year as his blockbuster franchise in 2008.
Pattinson gives a remarkably restrained performance as the famously eccentric artist, even if he does look fabulous in the mustache. Somewhere around the time of filming or shortly afterward, he entered into a relationship with Twilight co-star Kristen Stewart, although that ended badly and publicly when she cheated on him. Dali was never confirmed to be gay, which might explain the choice of a straight man to play him.
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18. Daniel Day-Lewis - My Beautiful Laundrette
Daniel Day-Lewis, with his unmistakable voice and presence, is probably best known for his terrifying performance in 'Gangs of New York.' His turn as a gay man in 'My Beautiful Laundrette' is less well-known, but it was captured on film back in 1985; a full eleven years before he married Rebecca Miller.
'My Beautiful Laundrette' is an oddity of a film, shot on a shoestring budget and depicting relations between the British and Pakistani communities in England during Margaret Thatcher's term as Prime Minister. The description makes it sound like a drama, and it easily could have been, but it's actually a comedy. The two main characters, one of which is Day-Lewis' Johnny, are old school friends who meet up years later, set up a business as a laundrette service and fall in love against the odds.
19. Keanu Reeves - My Own Private Idaho
It's easy to criticize or mock Keanu Reeves. Like Jared Leto, he's an actor who's also tried his hand as a rock musician with his band 'Dogstar,' and endured difficult times with rowdy audiences. He's also unfairly seen as a one-note actor, owing largely to his habit of picking either 'surfer guy' roles in 'Bill and Ted' and 'Point Break' or stoic roles in 'The Matrix' and 'Constantine' that don't require much in the way of acting.
His performance in 'My Own Private Idaho' is the perfect answer to that criticism. Reeves played Scott Favor in the movie, with River Phoenix opposite him. The script was loosely based on Shakespeare's 'Henry IV,' but with a gay twist that was years ahead of its time and prompted some controversy on its 1991 release. It was a modest success at the box office, but has gone on to become a cult classic.
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20. Will Smith - Six Degrees of Separation
Will Smith is another actor who doesn't get enough credit for his ability to play across genres. He's stereotyped as 'The Fresh Prince of Bel-Air,' a role which was close to his real-life personality, and also got tarred with the sci-fi brush by doing 'Independence Day,' 'Men in Black' and the critically-panned 'Wild Wild West' in quick succession. That means many people gloss over his role as Paul in 1993's 'Six Degrees of Separation.'
Smith is famously married to Jada Pinkett-Smith, and has been since 1997, but in this film, he was the mysterious 'Paul,' a serial conman who professed to be rich and straight but was actually poor and gay. The film is based on a Pulitzer-Prize winning book by John Guare, which is itself based on the real-life story of professional fraudster David Hampton.
21. Hilary Swank - Boys Don't Cry
It's no surprise that we're seeing so many fantastic character actors on this list; not every actor is capable of portraying someone of a different sexual orientation convincingly, but great performances come naturally to Oscar winner Hilary Swank. Swank has actually picked up 'Best Actress' twice at the Academy Awards, and the first of them was for 1999's 'Boys Don't Cry.'
In the film, she plays Brandon Teena, a trans man. Swank is utterly androgynous in her performance, and as a comparative unknown at the time the audience wouldn't have known for sure whether they were seeing reality or fiction. Brandon Teena really existed, and the film is his harrowing story. It's gritty stuff, and difficult to watch at times, but Swank is simply phenomenal in the part. In reality, at the time of filming she was married to Chad Lowe.
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22. Daniel Craig - Infamous
There's a connection here with a performance we've already looked at. Philip Seymour Hoffman, as you'll remember, played Truman Capote in his biopic, which focused on the author's fascination with the life and murders of Perry Smith. In 2006's 'Infamous,' Craig actually played Smith, a conman, a thief and a killer.
Craig has been playing James Bond on movie screens since 2005, and if he does stick around for the 25th Bond film in 2020, he'll celebrate 15 years in one of the most famous parts in cinema. In some respects, there are similarities between Bond and Smith; both of them employ deception as a day-to-day habit and kill people who get in their way. Bond has a definite way with the ladies, but it was always about the men for Smith, and Craig had no difficulty in showing that on screen.
23. Eric Stonestreet - Modern Family
If you've never come across this piece of information before, this might shock the 'Modern Family' fans among you. Eric Stonestreet, who plays the fabulously and flamboyantly gay Cameron Tucker in the show, is not gay in real life. The over-the-top camp part seems to come as second nature to Stonestreet, who's delighted millions with his performances, but it's all just acting.
Stonestreet isn't married in real life, and has stated that people just assume he's gay, and even feels it may have limited his romantic prospects. He's even gone as far as declaring himself 'openly straight' in the hope that people get the hint. He is, however, a keen advocate for gay rights, having felt loved and accepted by the gay community ever since he accepted his most famous role. The part has been good to him in return; so far, it's brought him two Emmy Awards.
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24. Paul Rudd - The Object Of My Affection
Paul Rudd is an actor who just seems to get on with things quietly; he has a list of credits that rivals any Hollywood A-Lister but doesn't seem to want or receive the same level of acclaim as many of his contemporaries. He's been married to Julie Yaeger since 2003, but a few years beforehand he won our hearts with a charming performance in 'The Object of My Affection' in 1998, playing Jennifer Aniston's gay best friend, George.
Rudd had textbook 'boy next door' looks in his younger years, which made him the ideal choice for romantic comedies, and this film was no exception. The smash-hit movie sees Aniston's character decide to raise a child with George despite the fact he'll never romantically love her, along with all the trials and tribulations that the situation presents.
25. Colin Firth - A Single Man
Colin Firth has been making women swoon ever since he gave us the definitive version of Mr. Darcy in 'Pride and Prejudice' in the 1990s; a role which he parodied to further acclaim in the 'Bridget Jones' series of films. Outside of the romantic performances, Firth is a highly accomplished actor, capable of giving a convincing portrayal of any character. 2009's 'A Single Man' is a textbook example of that.
In the movie Firth plays George Falconer, a depressed and suicidal professor struggling to come to terms with the death of his partner in a car accident. It's a bleak and dark film high on drama, which called on every bit of Firth's skill. He was rewarded with an Oscar nomination, but unfortunately wasn't able to claim the award, which went to Jeff Bridges that year for 'Crazy Heart' instead.
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26. Robin Williams - The Birdcage
Robin Williams had a rare and unique talent for both comedy and drama, drifting effortlessly between both and bringing audiences laughter and tears on a regular basis. He left us too soon and is still greatly missed by his fans. 'The Birdcage' was a particular triumph for Williams, a film with a mostly-comedy theme which still managed to tug on the heartstrings occasionally.
In the movie, Williams played Armand Goldman, the long-suffering better half of Nathan Lane's Albert. The 1996 film is fondly remembered by audiences for Gene Hackman's shocking appearance in drag, but it's still Williams who got most of the best lines as you'd expect. What many people don't know is that 'The Birdcage' is a remake; it was originally an Italian-French movie called 'La Cage aux Folles,' which was released almost twenty years earlier.
27. Christopher Plummer - Beginners
'Beginners,' released in 2010, is one of those romantic comedy-drama films which will have you laughing most of the way along, but then reduce you to tears when you least expect it. It tells the story of a man who lives most of his life in the closet, going so far as to get married and have children, only to finally accept his sexuality towards the very end of his life. Christopher Plummer is in the lead role as Hal and gave a performance which netted him the 'Best Supporting Actor' award at the 2011 Oscars. Ewan McGregor, who we've seen on this list already, also gives a star turn as Hal's son in the lead role.
The movie is played for laughs but comes with a heavy dose of truth; it's the work of writer and director Mike Mills, whose own father came out at the age of 75 after the death of his mother. Plummer is mesmerizing on screen, and utterly deserving of all the acclaim that came with the part.
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28. Ian Somerhalder - The Rules of Attraction
Before Ian Somerhalder stole millions of hearts in 'The Vampire Diaries,' he was giving a compelling performance as a conflicted gay man in 'The Rules of Attraction,' an onyx-black comedy based on a novel by Brett Easton Ellis, which made it to the big screen in 2002. The film plays with the conventions of a typical teenage 'coming of age' movie, in which the characters have to actually face the consequences of their actions.
Somerhalder's character Paul is hopelessly in love with his best friend Sean, but no amount of subtle hinting can get the message through to Sean, who is completely straight and wouldn't be interested anyway. The film was primarily a vehicle for James Van Der Beek, who was at the peak of his fame after his run in 'Dawson's Creek,' but it was arguably Somerhalder who really stole the show.
29. Tracy Morgan - The Longest Yard
It's difficult to really say whether this was a sensitive and balanced performance, or just a caricature of a stereotypical prison inmate. Tracy Morgan appeared in the Adam Sandler movie 'The Longest Yard' as transgender inmate Ms. Tucker, a bit part which was played for laughs and didn't do much for the furthering of gay parts on film.
Morgan is probably better known and appreciated for his work on 'Saturday Night Live' among other films, and 'The Longest Yard' wouldn't be considered to be among the highlights of his career. The film is what you'd expect from Adam Sandler; a sports comedy which is crammed full of as many cameos from as many famous faces as he could find. It was popular with audiences, going on to double its budget at the box office, but it wasn't well-thought-of among critics.
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30. Dennis Quaid - Far From Heaven
Dennis Quaid, the Quaid brother who didn't go on the run from the police while claiming that Hollywood assassins were coming to get him, has worked solidly in Hollywood for the past thirty years. In real life he was married to Kimberly Buffington until 2018, but in 2002 he appeared in cinemas as Frank Whitaker in 2002's 'Far from Heaven'; a married man who's living a life of repressed homosexuality.
It's a dark film, set in a time when homosexuality was a criminal offense, and men like Quaid's character sought out sham marriages to keep suspicion away from themselves. Unable to come to terms with who he really is, the character seeks out alcohol and prostitutes to numb the pain, which ends about as well as you suspect it would. The movie is an allegory for the general conditions that existed in 1950s America, and also boasts a stellar performance from Julianne Moore.
31. Josh Brolin - Flirting With Disaster
'Flirting with Disaster' would make a great title for Josh Brolin's autobiography; the actor has led a colorful life, with three marriages, two divorces and several run-ins with the law. It's also the title of the 1996 movie in which he appeared as Tony Kent, a gay federal ATF agent who actually seems more fluid about his sexuality as the film progresses.
This is another jet-black comedy, which centers on a young man who goes in search of his biological parents after having children of its own. That doesn't sound like the premise of a comedy, and it largely isn't, with the absurdity of some of the events that come later providing the laughs. Brolin's part in the film isn't huge; it's Ben Stiller and Patricia Arquette who have their names up in lights, but he gives a credible performance in the scenes that he's in.
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32. Chris Cooper - American Beauty
Given recent events, it now seems astonishing that there was a major role as a closeted gay man living in denial in 1999's 'American Beauty,' and it wasn't Kevin Spacey's character. That part actually went to Chris Cooper, who played a retired military officer named Colonel Frank Fitts. He wasn't only in denial about his sexuality; he was also homophobic to the point of being aggressive.
Cooper's role in the film isn't huge, but it stands out among the ensemble cast of the wildly popular and successful film. 'American Beauty' is part drama, and part social commentary; it explores the themes of masculinity, female empowerment and the emergence of gay pride at the turn of the century. It went on to score the premier trio of awards at the Oscars; 'Best Picture,' 'Best Actor' and 'Best Director.' It also picked up 'Best Original Screenplay' and 'Best Cinematography.'
33. Greg Kinnear - As Good As It Gets
On the one hand we could criticize Greg Kinnear's character in 1997's 'As Good as It Gets' for being written as the stereotypical gay artist (there's a constant insinuation in films that people who are interested in the arts are gay), but Simon Bishop is played with such heart by Greg Kinnear that it would feel wrong to do so. Kinnear serves as the movie's more sympathetic male lead, a stark contrast to the obnoxious main character Melvin, who's played with verve by Jack Nicholson.
The movie is a light-hearted romantic comedy with Nicholson's character hopelessly in love with Helen Hunt's, and it takes a gay man to get beaten up, lend him his dog and teach him the error of his ways before he finds the courage to tell her. There are several cliché boxes being ticked over the course of the film, but it's all done in good humor.
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34. Jada Pinkett-Smith - The Women
Anything Will Smith can do; his wife can do better! We've talked about Will's strong performance as Paul in 'Six Degrees of Separation,' and now here's Jada Pinkett-Smith trying her hand at a gay role in 2008's 'The Women.' She plays writer Alex Fisher, in a movie which has an entirely female cast and doesn't show any men at all on screen for its entire duration.
The film was supposed to be a celebration of womanhood but was savaged by critics on its release. It was a modern take on a film of the same name which was released in 1939. Many of the criticisms focused on the idea that many of the changes from the original felt forced; nothing more so than making Pinkett-Smith's character a lesbian. While many of the performers on this list received Oscar nominations for their portrayal of gay characters, poor Pinkett-Smith found herself making the shortlist for the Razzies.
35. Emily Blunt - My Summer Of Love
Bold, beautiful and years before its time 'My Summer of Love' will be a film that the majority of readers won't be familiar with. It's a low-budget British film from 2004 which never had a major cinema release and was released years before Emily Blunt was famous. This is, in fact, the first movie she ever appeared in, at the age of 19.
'My Summer of Love' is a lesbian twist on the classic tale of a rich person and a poor person meeting and falling in love, then fighting to overcome the social barriers that exist between them. It's a movie that feels frank and honest, which treats the lesbian relationship between its main characters as incidental to the main plot rather than central. They're two people in love who just happen to be gay. The gay magazine Autostraddle considers this to be 19th in the top 100 lesbian movies of all time.
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36. Chiwetel Ejiofor - Kinky Boots
There are two things about this movie that are startling to discover. Firstly, Chiwetel Ejiofor looks amazing in drag. Secondly, this outrageous British-made comedy-drama is based on a true story. The film is about a shoe factory which is facing closure until Charlie - a narrow-minded and very straight factory owner - meets Ejiofor's drag queen Lola. Lola persuades him to start making specialist footwear for drag queens, and hilarity ensues.
Ejiofor plays the character with great relish, and we suspect he had a lot of fun both on camera and between takes in the role. Since the movie was released, it's gone on to be adapted as a musical and has visited Broadway. Sadly, Ejiofor has not yet so far been persuaded to return to the role. We'd love to hear him release his version of the movie's title track as a single.
37. Julianne Moore - The Kids Are All Right
When Hilary Swank turned up on this list, it was inevitable that Julianne Moore would soon follow. The lookalike actresses have a running joke about sharing jobs and having similar careers, so of course Moore has played a gay character on screen as well! In fact, she's done it several times over, but the pick of all of her gay and bisexual roles is probably Jules in 2010's 'The Kids Are All Right,' which saw her nominated for a Golden Globe.
The movie is a comedy-drama but is especially notable for being the first mainstream movie that depicted a same-sex couple raising children. We've come a long way in the past decade! Moore's character in the film is a bored housewife who starts an affair with a male gardener, which is a nice twist on the old stereotype. Various publications, including The Independent newspaper in the UK, named it as the best film of 2010.
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38. Jonathan Rhys Meyers - Velvet Goldmine
If you're going to play a gay or sexually ambiguous character once in your career, you might as well push it as far as possible! We imagine that's the thought that occurred to Jonathan Rhys Meyers when he signed on the dotted line to play Brian Slade in the glam-rock drama 'Velvet Goldmine' in 1998.
As Slade, Meyers reaches a level of androgyny that would make David Bowie jealous, and a pinnacle of flamboyance that would make Liberace blush. He absolutely embodies the character of a sexually fluid 70s rock star and performs so naturally that sometimes you wonder if he's acting at all. The plot of the film is loosely based around the classic 'Citizen Kane', which was always likely to mean it had a tight narrative and would receive critical acclaim. It got plenty of that and marked Meyers out as a rising movie star.
39. Joshua Jackson - Cruel Intentions
1999's 'Cruel Intentions' is an ambitious movie which just about manages to be less than the sum of its part. The film was intended as a vessel for Sarah Michelle Gellar, who was at the peak of her 'Buffy the Vampire Slayer' fame. It's based on an 18th-century French novel titled 'Les Liaisons Dangereuses,' but re-imagines all the characters as wealthy, bratty American high-schoolers.
As a consequence of that, Joshua Jackson's character Blaine Tuttle becomes a throwaway stereotype; he's a token gay character who's used firstly to be catty, and then secondly to seduce and entrap a straight-but-questioning character with the intention of blackmailing him. As Jackson's is the only truly gay character in the film, it's not a flattering portrayal of the community. The general critical consensus of the movie is that it means well, and it tries hard, but too much of the text's heart has been lost by changing the period and location.
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40. Michael C. Hall - Six Feet Under
Anyone who remembers the HBO series 'Six Feet Under,' which ran for five seasons in the early 200s, will be familiar with Michael C. Hall's portrayal of the gay funeral director David Fisher. He was one of the two leads of the show, alongside Peter Krause. It was one of the earliest examples of a character whose homosexuality isn't their sole purpose; it's treated as normally as the heterosexuality of the other characters, which was ahead of its time twenty years ago.
Hall's character has only recently accepted that he's gay as the series begins, and the audience live his journey with him over the years to come as he wrestles with his identity, supported by his long term partner Keith. In the series' final episode, when the futures of all the characters are foretold, it's revealed that David and Keith eventually marry in a future beyond the end of the series.
41. Annette Bening - The Kids Are All Right
When we were talking about Julianne Moore's role in 'The Kids Are All Right' earlier on, we should have mentioned one critical detail; a straight woman also plays her partner. It's Annette Bening in the role of Nic; a lesbian obstetrician whose devotion to her work leaves Moore's character bored at home. That's what pushes her bisexual partner towards her affair with the male gardener, and Bening's character has to deal with the fallout.
Much like Moore, Bening received a lot of acclaim for the role, including a Golden Globe of her own. The much-celebrated actress will have added that to a whole trophy cabinet of awards which is only now missing an Oscar; she's been nominated four times but is yet to win an award. She does, however, have her own star on Hollywood's Walk of Fame, so we're sure she doesn't mind.
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42. Armie Hammer - J.Edgar
We could have put Armie Hammer forward for two roles here, but we're just about giving the nod to his part as Clyde Tolson in 2011's 'J. Edgar', although it's a close call with his other major gay performance as Oliver in 2017's 'Call Me by Your Name.' The latter film is a heartbreaking and beautiful tale of sexual experimentation on a Summer holiday, but the gravitas and subject matter of 'J. Edgar' just wins out.
There is enormous controversy about J.Edgar Hoover's sexuality, and it never has (and probably never will) explicitly be confirmed that he was gay, but his lawyer Clyde Tolson was. Tolson was the main beneficiary of Hoover's will, and also accepted the US flag that was placed on his coffin at his funeral. Hammer's performance in both movies is incredible, but he's married to Elizabeth Chambers in real life.
43. Heather Graham - Gray Matters
Despite a cast that included Heather Graham, Alan Cumming, and Sissy Spacek, 'Gray Matters' struggled to achieve a wide cinema release and finished its cinema run having made less than $1m in takings. In short, it was a disaster. That's a shame, as it's a fun and gentle comedy with a poignant story and likable characters.
The long and short of the script is that Graham's character Gray Baldwin is trying to set her unlucky-in-love brother up with a woman, only to fall in love with the woman herself. Her brother and her intended target fall in love and agree to get married, only for Gray and the bride-to-be to kiss on her hen night. A voyage of self-discovery ensues with jokes and sadness included, all of which is performed with authenticity and heart by Graham. It's apparently based on the real-life tale of writer and director Sue Kramer's sister.
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44. Macauley Culkin - Party Monster
The life and times of Macauley Culkin have been stranger than the script of any movie ever written. From his child stardom in 'Home Alone' to his friendship with Michael Jackson, his arrests and legal troubles and his multiple 'retirements' from acting (and subsequent returns), he's seen his fair share of highs and lows. His desire to shake off his 'Home Alone' typecasting have seen him try a number of experimental roles. The part of Michael Alig in 2003's 'Party Monster' was one such experiment.
This was Culkin's first movie role in nine years, and his first as an adult. It didn't do well. The real-life Michael Alig was gay, but he was also a party-obsessed socialite who got deeply involved in drugs and ended up going to jail for murder, with no redemption angle or seemingly any likable traits. Because of that, a biography of him was never likely to appeal to audiences, and it didn't. It returned less than $1m of a $5m budget, and Culkin went back to the drawing board.
45. Seth Green - Party Monster
It wasn't just Macauley Culkin trying to expand his acting horizons in 'Party Monster' (and then probably wishing he hadn't bothered). Seth Green was in on the act as well. In Green's case he played the part of James St James, the cross-dressing member of the so-called 'Club Kids' who went on to become a writer and 'famous for being famous' celebrity years after the club scene he was part of ended.
It was St James who wrote the original book 'Disco Bloodbath' upon which 'Party Monster' was based. Green, straight in real life but also known for being clean-cut, was always a strange choice to play him on screen. If nothing else, he managed to look fantastic in the costumes, and he's since gone on to have a fantastic career as a producer and director, as well as lending his voice to Chris Griffin on 'Family Guy.'
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46. William Hurt - Kiss Of the Spider Woman
You probably know William Hurt best for 'Body Heat,' 'Altered States,' 'Syriana' and his appearances in the 'Avengers' series of films, but he also put in a terrific and powerful performance as Luis Molina in 1985's 'Kiss of The Spider Woman.' Although the name might make it seem like another superhero-themed role for Hurt, it's anything but.
The movie sees him play across from screen great Raul Julia in a movie that contains very few other characters. Hurt's character is a transgender woman, serving time for illicit sexual encounters, and an unlikely friendship develops between her and Julia's battle-hardened left-wing revolutionary. The friendship eventually evolves into a romance that can never be, with Hurt beguiling in his role, wholly committed to the character and making an emotional connection with the audience. This is a dark, disturbing and yet somehow inspiring film, which just wouldn't work without the greatness of Hurt's work.
47. River Phoenix - My Own Private Idaho
We spoke about Keanu Reeves in 'My Own Private Idaho' earlier on in this list, and the fantastic job he did with his performance in the film, but it would all have been to no avail if he didn't have River Phoenix opposite him to play off from. Phoenix, as he always was in everything he did, is totally believable as Mike Waters. The character had a huge impact on gay people and gay culture upon the film's release and represented one of the first depictions of a gay man as a tough guy and an alpha male.
Phoenix always had an element of street-smarts about him, and he brings that to the role, giving life and character to Waters; a street prostitute who treats his occupation as a job and doesn't recognize himself as being gay. The character also has a troubled relationship with drugs, which is a tragic parallel with Phoenix himself.
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48. Cher- Silkwood
Cher's acting career, much like fellow pop superstar Madonna's, is sometimes dismissed as being a by-product of her musical fame. Most people don't think of her as a serious actress, but in doing so, they look past quite a compelling body of work which includes both 'Mask' and this highly effective performance in 'Silkwood.' Both films are biopics, but it was the way that Cher effortlessly slipped into the role of Karen Silkwood's lesbian friend Dolly (based in Dusty Ellis) that really convinced us she could act.
The real-life person that Cher's character was based on was an unstable one, who once took people hostage at gunpoint in a nursing home. Cher is able to portray a little of her mania here, most notably when she draws a funeral parlor beautician into the home she shares with Silkwood and makes a complicated situation worse. Cher was nominated for a 'Best Supporting Actress' Oscar but was overlooked in the night of the ceremony.
49. Richard Jenkins - Flirting With Disaster
Remember earlier on, when we talked about Josh Brolin's part as a gay ATK agent in 'Flirting with Disaster'? Brolin played the part of Tony Kent, and his ATK partner on the job is also his romantic partner; Paul Harmon, played by Richard Jenkins.
Brolin's part wasn't central to the movie, and Jenkins' is even smaller. His main function is to get accidentally dosed with drugs at a party, setting off the chain of events that leads to the movie's conclusion. Perhaps the biggest positive of the two parts is that the fact they're gay doesn't matter to the plot; it's an incidental fact of their lives. Harmon is the only notable gay part of Jenkins' long career, although he does crossover with Michael C. Hall who we also looked at earlier; both were on the cast of 'Six Feet Under' for the duration of the show.
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50. Cillian Murphy - Breakfast On Pluto
Cillian Murphy must be one of the hardest working actors in Hollywood or on television; it feels like he turns up everywhere all the time. One of the roles you're less likely to have seen him in, though, is 2005's 'Breakfast on Pluto', where he's absolutely riveting as the transgender character Patrick, also known as Kitten Braden.
'Breakfast on Pluto' is a small British independent film, with Murphy's character fleeing from the oppression of conservative Ireland to both search for her mother and explore her own identity in the bright lights of London in the 1970s. There's plenty of drama in the script, although it presents as a comedy and has undeniably comic moments. Murphy received a Golden Globe nomination for his performance. He took the part seriously, hiring the services of a drag queen to give him one on one training and also take him out clubbing so he could get a better feel for gay culture.

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