Gay Best Friend: Todd Cleary (Keir O'Donnell) in "Wedding Crashers" (2005)
Wednesday, August 18, 2021 at 10:32AM A series by Christopher James looking at the 'Gay Best Friend' trope
Was Todd (Keir O'Donnell) the earliest inspiration for Gru from "Despicable Me?"I don’t love to complain (okay, sometimes I do). Most of the times I write this column to understand how gay representation in mainstream film has changed and evolved over the decades. Each shortcoming could be seen as another toe that LGBTQ+ characters stuck through the door of mainstream society. However, not all representations are good. Especially in the late 90s and early/mid 2000s, male focused comedies used gay characters as particularly malicious punchlines. As cartoonish as these characterizations are, they did paint a horrifying portrait of gay life to straight people. To gay people, these characters also served as a vision of what straight America hated about them.
My dark confession is that I love Adam Sandler comedies. They remind me of being an immature teenager and immediately bring back the sense memory of my hometown and a specific period in my life. Yet, these films were often the main source of these mockeries of gay life. (Though Sandler could be an equal opportunity offender, making himself the butt of the joke, too). Other mainstream comedies followed this formula to diminishing (and more demeaning) returns. The biggest R-rated comedy of this time was Wedding Crashers. The film grossed $205 million domestically (only to relinquish this title later to The Hangover 1 and 2) and was a word of mouth hit.
Today, the film’s success feels completely wild...
It’s not just that the movie is offensive, homophobic and mysoginistic (it’s all of those things), but it doesn’t even have that many jokes. In my memory, at least the first hour was a mile-a-minute laugh riot followed by a dour second hour. On rewatch, that isn’t even true. The first-half sets up the unpleasantness that engulfs and dominates the entire film. In short, it’s an unforgivable slog.
I’m getting ahead of myself. This column isn’t called “ruin your favorite bro comedy from the 2000s” (even I wouldn’t read that). So who is the gay best friend (more like gay butt of the joke)? That would be Todd (Keir O’Donnell), the black sheep of the Cleary family.
Talk about a dinner party from hell.
Claire Cleary: Actually Todd is an amazing painter. He's going to the Rhode Island School of Design.
John Beckwith: Wow, that's a great school. Congratulations, Todd. That's really impressive. RIS-D!
Todd Cleary: Yeah, Dad - Dad always thought I'd be a political liability...
[getting angry]
Todd Cleary: ...in case he ever ran for President.
Secretary Cleary: Now, now Todd. Actually, truth be told, polling shows that a majority of the American people would ultimately empathize with our situation.
Todd Cleary: [sharply, raising his voice] What IS our situation, Dad?
Grandma Mary Cleary: You're a homo.
We meet Todd as John (Owen Wilson) and Jeremy (Vince Vaughn) are doing recon on the wedding of Christina Cleary (Jennifer Alden). Her Father is the U.S. Secretary of the Treasury, William Cleary (Christopher Walken). As they crash the wedding, John and Jeremy flirt with two of Christina’s sisters - the chill Claire (Rachel McAdams) and “stage-five clinger” Gloria (Isla Fisher). They make an impression and are invited to a weekend at the Cleary’s estate following the wedding. With jet black hair, a scowl and a bit of a hunchback, Todd is coded first as a sort of grotesque gargoyle and second as queer. This is only further underlined when he’s presented next to his family. Secretary Cleary has three beautiful daughters and one son that spells only trouble for him. The movie never defines Secretary Cleary’s politics, but needless to say John McCain is in attendance at Christina’s wedding.
The first dinner of the weekend clearly states how Todd is viewed within his family. Even when the conversation turns to an interest or character trait of his (i.e. painting), the script reverts back to the easy joke. We don’t need to get to know anything about this character because the movie thinks we already know enough - he’s gay and thus a freak. Todd labels himself as a “political liability” that could keep his Dad from moving up the ranks. The best compliment that William can come up with is that people would “empathize with their situation.” The situation in question? Dealing with a gay kid. Grandma Cleary (Ellen Abertini Dow) very much doesn’t want to deal with their “situation.” Almost every word out of her mouth is “homo,” said in the most disgusting sneer. Everyone in the Cleary family treats Todd somewhere between ambivalence and disgust. The joke is always on him, as if the filmmakers think we’re going to fall on that same spectrum too.
Jeremy (VInce Vaughn) gets a surprise from a different member of the Cleary family.
Todd Cleary: I made you a painting. I call it "Celebration." It's sexual and violent. I thought you might like it.
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Todd Cleary: We had a moment at the dinner table didn't we?
Jeremy Grey: No! No! We did not have a moment at the dinner table, Todd!
Things only go from bad to worse as day turns to night. After Jeremy pries himself away from Gloria, he retires to bed only to wake up to a surprise. Todd wakes Jeremy up and presents him with a “tasteful nude” painting that he did of him. The whole scene escalates with Todd trying to force himself on top of Jeremy, while Jeremy reacts with utter fright. There are so many ways to slice what’s so offensive about this. It reinforces this idea that gay men will act aggressively and try and “turn” straight men. These “real men” should fear this abnormal man who can only think with his dick. Similarly, the film thinks its funny that Jeremy is being pressured into having an unwanted gay encounter. The next morning, Jeremy tells John he felt like “Jodie Foster in The Accused,” where Foster played a rape victim. By my count, sexual assault is funny, particularly because it happened between two men. Good work to all involved.
I don't think Jeremy hung that painting in his apartment following the weekend.
When John and Jeremy are kicked out of the Cleary house, we leave Todd and many of the side characters behind. As they are leaving the house, Jeremy gets one last jab in to Todd. He’s going to keep the painting “because it was a gift.” For roughly 45 more minutes, John wallows in his feelings until going after his happy ending with Claire. Jeremy accepts that he maybe likes Gloria’s craziness and proposes to her. Everything is right with everyone. Yet, punchlines like Todd don’t get happy endings. Other comedies took homophobic jabs at their token characters. Still, Wedding Crashers felt like a particularly egregious example of this troubling trend.
There’s a reason this movie was a hit in 2005, and it’s not just because people didn’t care about misogyny or homophobia. It’s a good idea for a movie. The idea of a movie about wedding crashers is inherently funny. These people come for the good parts of a wedding - the booze, the women, the lower inhibitions, the dancing - but stay too long and get wrapped up in the bad parts of a wedding - family drama. Unfortunately, the men are just assholes through and through and the Cleary family is so one-dimensional. Each family member gets one joke and one characteristic. Isla Fisher is crazy. Rachel McAdams is pretty. Bradley Cooper is an asshole. The Grandma says homo A LOT. There’s never another joke or another level to any of the characters, yet they all feel like they’re begging for another dimension.
Every joke relies on stereotypes, rather than subverting stereotypes. What would happen if the men were outmatched by the women’s wits? What would happen if the Cleary’s political positions were challenged (or at least defined)? What would happen if the movie didn’t ditch having fun after the opening monologue? For a movie that was widely considered R-rated debaucherous fun, no one seems to be having any fun. Weddings are supposed to be fun.
Previously in Gay Best Friend
pre stonewall
- Plato (Sal Mineo) in Rebel Without a Cause (1955)
- Sebastian Venable in Suddenly Last Summer (1959)
- Calla Mackie (Estelle Parsons) in Rachel Rachel (1968)
post stonewall
- Erich (Norbert Weisser) in Midnight Express (1978)
- Toddy (Robert Preston) & Squash (Alex Karras) in Victor/Victoria (1982)
- Dolly Peliker (Cher) in Silkwood (1983)
- Buffy (Charles Grodin) in Woman in Red (1984)
1990s and the 2000s
- Tim (Nathan Lane) in Frankie & Johnny (1991)
- Hedy (Jennifer Jason Leigh) & Graham (Peter Friedman) in Single White Female (1992)
- Sammy Gray (Steve Zahn) in Reality Bites (1994)
- Gareth (Simon Callow) and Matthew (John Hannah) in Four Weddings and a Funeral (1994)
- Jane (Whoopi Goldberg) in Boys on the Side (1995)
- Sterling (Patrick Stewart) in Jeffrey (1995)
- Christian (Justin Walker) in Clueless (1995)
- Cleo (Queen Latifah) in Set it Off (1996)
- George Downs (Rupert Everett) in My Best Friend’s Wedding (1997)
- Simon (Greg Kinnear) in As Good As It Gets (1997)
- George Hanson (Paul Rudd) in The Object of My Affection (1998)
- Bill Truitt (Martin Donovan) in The Opposite of Sex (1998)
- Buck (Mike White) in Chuck & Buck (2000)
- Michael (Stuart Wells) in Billy Elliot (2000)
- Robert (Rupert Everett) in The Next Best Thing (2000)
- Patti (Sandra Oh) in Under the Tuscan Sun (2003)
- Michael (Robin de Jesús) in Camp (2003)
- Damian (Daniel Franzese) in Mean Girls (2004)
- Nigel (Stanley Tucci) in The Devil Wears Prada (2006)
- Wallace Wells (Kieran Culkin) in Scott Pilgrim vs the World (2010)
- Brandon (Dan Byrd) in Easy A (2010)
- Patrick (Ezra Miller) in The Perks of Being a Wallflower (2012)
the now
Reader Comments (4)
I understand that a column focusing on "ruining" bro comedies would be obnoxious in a holier-than-thou sort of way, so I appreciate that you pointed out your reservations about going in that direction with this, but this movie frankly deserves that treatment. You nailed it: it's not even "just" that it's homophobic and misogynistic as hell, it's also not even funny in the way that certain other movies of its type can be that allows us to (somewhat) forgive their outdatedness. I hate to use the "boys will be boys" excuse for other movies, but it feels at least somewhat warranted for movies like Wayne's World or, yes, a few Adam Sandler movies from that era, because while they may contain a few jokes that are cringey by today's standards, their overall nature is goofy and lighthearted. The insensitive jokes in those films read more as careless ignorance than anything resembling actual maliciousness.
Wedding Crashers, on the other hand, actually feels mean-spirited. I don't think you can chalk it up to simply being a product of its time in the way that you can for a lot of other films of its type. I saw it in theaters, and it felt mean-spirited even then. It's not just a "bro" movie; it's a bully movie. I completely agree that its enormous success feels baffling in retrospect, particularly because it was kind of baffling even in 2005. And what's more, it wasn't just a box office hit. It actually got mostly good reviews too. Rolling Stone even placed it on its list of top 10 movies of the year (not that I put stock into them, but given what else they put on the list that year, it feels downright bizarre).
In any case, don't feel bad about going on the offense against this movie. It deserves that kind of scorn, really.
I had forgotten this character completely, but then again I'd forgotten the movie almost completely. I remember disliking it and finding it very unfunny. With one exception: the scene where they track down Will Farrell and find him living the dream. He sits around all day in his underwear and a bathrobe watching cartoons on tv while his mother waits on him hand and foot. For about five minutes the film is hysterically funny, then it sinks back into its unfunny morass. Perhaps this scene seems funnier than it is because everything before and after is so dire.
I googled Wedding Crashers and discovered these depressing facts. It won the People's Choice award for Best Comedy (ok so what) and was nominated for a Critics Choice Award for Best Comedy.
Gay Best friend? Isn't he more like a butt of a joke?