In the world of film, it's always interesting to see how actors will take on a particular role, especially one that's intended to take them out of their comfort zones. Many performers decide to push themselves to the limit in order to achieve a performance that's Academy Award worthy, and we've seen truly mesmerizing performances because of this. Actors whom most didn't think were capable of playing the role end up knocking it out of the park, and their performances can catapult them to superstardom. It's one of the things that make each film an anticipated release, and seeing your favorite performers prove their doubters wrong is always a treat for moviegoers.
On the opposite side of the spectrum, however, are the people who prove doubters right and turn in performances that we wish they would've avoided altogether. The performers that you'll find on this list are straight men who elected to play a gay character, and most fans now wish that these roles went to other actors. This isn't to say that these individuals were completely terrible in the roles that we're discussing. This is simply meant to point out that these actors were better suited for other roles at the time, and that whoever cast them probably should've looked elsewhere for the right actor. Delivering a stellar performance is one of the harder things an individual can achieve, and despite the talent on this list, these men all failed in playing a gay character.
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15 Bradley Cooper - Valentine’s Day
When you think of Bradley Cooper, playing a gay character is probably the last thing that comes to mind, but he finds himself on our list for a reason. Bradley Cooper is an incredibly handsome man who's garnered a huge female following over the course of his successful career, but this hasn't stopped him from expanding his acting repertoire. In 2010, Bradley Cooper joined the ensemble cast of the film Valentine's Day, and he was tasked with portraying the character Holden Wilson.
Because of the immense amount of talent that was involved with the project, Bradley Cooper gave a decent-but-forgettable performance as the gay character. Regardless of how you feel about his performance in the film, Valentine's Day proved to be a huge hit at the box office, and when the dust had finally settled on its theatrical run, Valentine's Day had pulled down $216 million.
14 Robert De Niro - Stardust
Robert De Niro is one of the few men on the planet who can genuinely be considered a living legend in the world of film, and he's given some of the most incredible performances that we've seen. But with a career that's spanned numerous decades, Robert De Niro has also found himself in movies that were less than stellar, making you question why he bothered to take the role in the first place.
In 2007, Robert De Niro appeared in the film Stardust, which was a film adaptation of the popular novel. Unfortunately for Robert De Niro and everyone else involved with the project, Stardust received a mediocre reception upon its release, and it's since become a mostly forgettable film. The film's $135 million box-office haul made it a financial success, but you'd be hard-pressed to find someone clamoring to give this film another go.
13 Jim Carrey - I Love You Phillip Morris
During the 1990s, Jim Carrey became the premier comedic actor on the planet, and he delivered some of the decade's most noteworthy comedic performances. Many of us grew up quoting his many catchphrases from his hit films, and he's received an incredible amount of praise over the course of his career. As the years went on, Jim Carrey found himself steering clear of comedic performances in favor of more dramatic roles, which has yielded a mixed bag of success.
In 2010, the film I Love You Phillip Morris was released in the United States. In the film, Jim Carrey plays a gay character named "Steven Russell," and his performance left a lot to be desired. He wasn't terrible by any means, but another actor could've been much better in the role. The film was a dud at the box office, and it only managed to bring home $20 million.
12 Diego Luna - Milk
After the release of Rogue One, actor Diego Luna became a recognizable face in Hollywood. Long before this, Luna was already pumping out high-quality work, and he was widely recognized for the incredible talent that he possessed. Eight years before Rogue One was released and dominated at the box office, Diego Luna co-starred in the film Milk, and the film boasted an incredibly talented cast. The film revolves around the rise of slain politician Harvey Milk, and Diego Luna was cast as a Jack Lira, Harvey Milk's lover.
While the film itself and the bulk of the performances in it received a ton of acclaim, we would be remiss if we didn't point out the fact that Luna's performance was a little over-the-top throughout the film. It wasn't terrible, but he really seemed to overdo his performance throughout the movie. Nevertheless, Milk was a massive success, and it went on to haul in $54 million at the box office.
11 Paul Rudd - The Object Of My Affection
Now that Paul Rudd is part of the Marvel Cinematic Universe, he's become a bonafide box-office star, but he had been successful long before taking on the role of the character Ant-Man. Rudd first came on the scene in the 1990s, and he's put together an incredible career so far, and he's built a massive following of fans that span the entire globe. He has a personality that resonates well with fans, and he seems like a genuinely nice guy.
In 1998, Paul Rudd co-starred in the film The Object of My Affection, and the film proved to be a modest success at the box office, pulling down $46 million. In the film, Paul Rudd played a gay teacher, and while he was pretty good in the role, we can't help but wonder who else could've played the character. Rudd is an incredibly handsome man who usually finds himself married to a beautiful woman in his films, so seeing him as a gay man is pretty bizarre.
10 Josh Brolin - Flirting With Disaster
Not only is Josh Brolin an incredibly good-looking guy who's been married to one of the hottest women in the history of Hollywood, but he's also usually found playing a tough-guy type of role in his films. It's for this reason that Brolin finds himself on this list after an appearance in the 1996 film Flirting with Disaster. Josh Brolin was already established in the film industry when he decided to take on the role of Tony Kent in the film, and seeing his character in a relationship with Richard Jenkins in the film is pretty funny.
Upon its release, Flirting with Disaster failed to do much of anything at the box office, and the film only managed to pull down a paltry 14 million dollars. Brolin is an incredibly talented actor, and while seeing him play something out of character is interesting, someone else would've been better suited for the role in the film.
9 Joshua Jackson - Cruel Intentions
Very few people remember this movie for anything more than its stellar soundtrack and the red-hot scene of Sarah Michelle Gellar making out with Selma Blair. In all fairness, Cruel Intentions wasn't a terrible movie at all; it just happened to have an amazing soundtrack and one of the hottest scenes of the '90s. What most people seem to forget is that actor Joshua Jackson played a gay character in the film. Then again, most people don't remember most of the intricate details of the film, to begin with.
This entry has more to do with the film itself as opposed to the actor because whoever wound up with the role was destined to be left in the dust. Perhaps another actor could've given a more memorable performance, but we have doubts that people would be more inclined to remember the role had it been someone else. Cruel Intentions was a relative success upon its release, though Jackson had other successful projects to rest his laurels on.
8 Keanu Reeves - My Own Private Idaho
Keanu Reeves has had a very successful career since breaking out in Bill & Ted's Excellent Adventure in the 1980s, and his success has spanned several different genres in the world of film. The biggest knock against Keanu Reeves is that he acts very similarly in all of his films, and while he wasn't giving his usual Ted performance, many people wondered if another actor would've been better suited for his role in the film My Own Private Idaho.
The critically acclaimed film had an amazing cast of actors, but it failed to achieve much of anything at the box office. Despite the critical acclaim that it received upon its release, the film will be best remembered as one of River Phoenix's final films before his untimely death. While Keanu Reeves did turn in a pretty good performance, another actor of River Phoenix’s caliber in the film could've taken it to the next level.
7 Philip Seymour Hoffman - Boogie Nights
Before he became an Academy Award-nominated actor, Mark Wahlberg was looking for his big break in the film industry, and that break finally came in 1997 with the release of the film Boogie Nights. Boogie Nights is perhaps the most criminally underrated film of the 1990s, and the ensemble cast and incredible script made for a truly great movie. Philip Seymour Hoffman was cast as the character Scotty in the film, and much like Diego Luna's performance in Milk, Hoffman's performance in Boogie Nights was usually over-the-top.
Scotty is a young man who works on the set of these pornographic films, and he falls in love with Mark Wahlberg's character, Dirk Diggler. In scenes where he doesn't speak too much, Hoffman is excellent. Thankfully, he dialed in this type of character to perfection when he delivered a stellar performance in the film Capote, which made Hoffman a household name.
6 Mike Myers - 54
The fact that Mike Myers isn't still a major player in the world of film is an absolute travesty, but this entry isn't meant to be a puff piece about how much we enjoyed his work. Myers has played a number of memorable characters over the course of his career, and in 1998, he played a gay character in the drama 54. Mike Myers has proven on countless occasions that he has great acting skills, but he just didn't feel right for this particular role.
The film received very negative reviews upon its release, and you have to wonder if the casting choices for nearly all of the roles could've played a factor in this. Myers just seemed out of place, and the film only managed to pull down $16 million, barely clearing its production budget. Even if another actor had played this character, though, we're sure that it would've done very little to save this film from being a disaster.
5 Sacha Baron Cohen - Bruno
Too much of a good thing can often be a bad thing, and when Sacha Baron Cohen decided to release a second mockumentary film, he learned a very hard lesson. Cohen's film Borat had taken the world by storm, and it went on to have massive amounts of success at the box office. Many people were excited for Bruno, but they ended up finding themselves incredibly disappointed at this bizarre film. Bruno managed to corral average reviews upon its release, but it still made $138 million at the box office.
With all of that said, Cohen would've been better off casting someone else as the lead character. The film just felt far too familiar to Borat, but it was far less interesting and far less funny than its predecessor. After the failure of the film, Cohen decided to stay away from this type of film, and we can’t imagine him doing another one anytime soon.
4 Tracy Morgan - The Longest Yard
Going back to the well and giving new life to an old film is an old Hollywood trick, and in 2005, Adam Sandler starred in a remake of the film The Longest Yard. This came at a time when Adam Sandler was still a huge box-office draw as indicated by the film's impressive haul at the box office. Despite receiving some mixed reviews, the $190 million made by The Longest Yard made it a certified hit. The cast was incredibly talented, but casting Tracy Morgan as the character Miss Tucker was a real travesty.
Regardless of which role he takes on, Tracy Morgan will always find a way to pack a ton of laughs. However, a man of his talents should've never been cast in this role, and it should've gone to someone else. Tracy made sure to bring the laughs, but it was a real disservice to him to have him cast as such a character.
3 Patrick Swayze - To Wong Foo
Much like the aforementioned Josh Brolin, Patrick Swayze had a gigantic female following that he had earned over the course of his career. He was an incredibly good-looking guy with a ridiculous amount of dancing skills to boot. The 1980s saw Patrick Swayze become a major player in Hollywood, and women couldn't get enough of him. No matter how much success you find in your career, though, you'll always find yourself making some poor choices in roles, and Swayze starring in the film To Wong Foo was an awful choice.
The film boasted a very talented cast, but it received mixed reviews upon its release. It wound up pulling down a solid $47 million at the box office, though most people wish that Swayze would've avoided doing the film altogether. For a man who has an incredible number of hit films under his belt, To Wong Foo will always feel like a rare blemish on an otherwise stellar career.
2 Ving Rhames - I Now Pronounce You Chuck & Larry
The second Adam Sandler film on this list cast Ving Rhames as an openly gay fireman, and the casting of Rhames seemed really out of place with the film. He's an immensely talented performer, and his casting was meant to be a juxtaposition of preconceived notions and reality. For those of you who remember this comedy, two best friends pretend to be gay in order to keep their benefits. It was meant to be a hilarious take on what should be a serious situation, but that didn't stop critics from ripping them to shreds.
But because the film was released during a period when Sandler was still popular, it still pulled down a whopping $186 million at the box office. Even though casting Ving Rhames as a gay character was meant to be hilarious, the movie itself made the entire thing quite forgettable. This is one movie we wish we hadn’t seen in the first place.
1 Mick Jagger - Bent
Mick Jagger is one of the most notorious ladies' men in the history of music, and few people on this planet who could ever picture him being gay, despite some rumors that have been circling since the 1970s. Then again, most people don't really think of Mick Jagger as an actor in the first place. Back in 1997, Mick Jagger was cast as the character Greta in the film Bent. The film was an adaptation of a play and is an otherwise forgettable film.
To give you an idea of the type of impact, or lack thereof, that Bent had, the film made less than $500,000 at the box office. In the film, Mick Jagger plays a gay character, and his casting was a major headscratcher. Since no one remembers this film, it's safe to say that almost anyone else would've been better suited for the role. They can't all be winners, and this film is a shining example of what a dud looks like.
Sources: IMDB, Boxofficemojo
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