Gay Best Friend: Peter Steinberg (Oliver Platt) in "Three To Tango" (1999)

A series by Christopher James looking at the 'Gay Best Friend' trope

Oliver Platt's boredom-induced hairstyle is far from the worst part of "Three to Tango."

Why did every member of Friends want to do a gay themed movie as their attempted jump to film stardom? Lisa Kudrow earned awards attention in the sublimely tart The Opposite of Sex, while Jennifer Aniston’s charm and chemistry with Paul Rudd nearly made The Object of My Affection work (okay, maybe not). Matthew Perry’s dreadful vehicle Three To Tango feels like the nadir of the Friends theatrical launching pads, gay-themed or otherwise. With a script forged in gay panic, the instantly dated comedy is short on charm and laughs. However, it has casts a bizarre spell as a hate-watch. It’s an insensitive film that is a strange reflection of 1998 attitudes towards the LGBTQ community and what types of vehicles could launch a film career.

For the purposes of this column, our entryway into this movie is through Oliver Platt’s Peter Steinberg. He’s the openly gay architect partner of Oscar Novak (Perry). Through a series of bizarre miscommunications that would’ve been vetoed by the Friends writer’s room, everyone starts to think Oscar is the gay partner and Peter is the straight one...

There are so many bad points where Perry’s straight character is poised as a “savior” or “exemplary” example of a gay person, which is bad enough. But there’s something particularly sad of watching Peter have his queerness erased.

Sadly, Peter is sidelined through most of the movie (why give your gay character anything to do in a movie about sexuality). So let’s break down the plot.

 It's a classic story of boy meets girl, girl thinks boy is gay, boy goes along with it for career gains.

As stated, Oscar and Peter are architects vying to win a bid to restore a historic Chicago museum. Right before their presentation, the secretary overhears they talking about “being partners” and “loving each other” and jumps to the conclusion that they are a homosexual couple. She immediately lets her boss, the womanizing tycoon Charles Newman (Dermot Mulrooney) know this piece of information, which he finds intriguing. An idea sparks in his head… not about the building contract in hand though. Charles is having an affair with a free spirited glassblower, Amy (Neve Campbell), and worries about her cheating on him. He comes up with a “brilliant” idea where Oscar, being a “gay man,” can stalk Amy and make sure she’s not being unfaithful. Since Oscar is “gay,” there’s no way he would ever make a pass at her.

Oscar obliges to attend Amy’s art show, only to fall immediately in love with her over a broken cab and nauseating tuna sandwiches. It’s not until later that he realizes that both Charles and Amy both think he’s gay. It’s a war between his head and his heart. His head wants him to play gay and keep in Charles’ good graces to get the job. Yet, his heart pines for Amy, the ultimate ‘90s depiction of a cool girl. Peter definitely believes Oscar should suck it up and play gay to achieve work success. However, Oscar makes it very clear that this arrangement is far from ideal for him.

 Never interrupt a gay dinner party without good reason, Oscar Novak (Matthew Perry).

Oscar Novak: I know. I mean, how could they think that? Me, gay? It's just so embarrassing and mortifying and....

Peter Steinberg: Humiliating.

Oscar Novak: Humiliating, yes! I mean, I don't get it. I don't see it. I'm just a regular, normal...insensitive asshole. But come on. You know what I mean, right?

Peter Steinberg: Oh, sure. When you say you're humiliated...you actually mean you're proud and unashamed.

Oscar Novak: No. It's not that. It's just--

Peter Steinberg: Being gay's not normal.

Oscar Novak: I don't think that. I have no problem with people being gay. I'm all for homosexuality… especially when it's between gorgeous women. But I'm not gay! I’m sorry. I didn't mean what I said before. What are you doing?

Peter Steinberg: I’m trying to decide...if I should recover gracefully from your insults...or kneecap you.

This is the lone scene where we really see Peter fight for himself against his friend. Him and Oscar are full of good-natured jabs, but Oscar certainly crosses a line a few times over in this scene. It happens during one of Peter’s dinner parties with his gay friends, so already Oscar is invading Peter’s turf. Even though Oscar is coded as liberal and accepting, he still associates being gay with embarrassment, mortification and humiliation. At least the movie gives Peter strength and moral high ground in this moment. It is wrong for Oscar to vent his frustrations this way, and Peter shouldn't be expected to bear the brunt of his selfishness.

A clunkier, yet well-meaning movie would use this as the starting point for Oscar’s eventual arc to a more accepting person. Three to Tango somewhat does that, but Oscar still feels some level of embarrassment to be considered gay by the end. That’s because the movie also feels a bit embarrassed to be about gay people. Peter is the only real gay character of note in the ensemble. All of Oscar’s time “pretending to be gay” is done hanging out with Neve Campbell. What if she had insisted they go to a gay bar so she won’t be hit on? Yes, the comedy would likely still be incredibly cringe. Still, at least the movie would've actually seemed like it wanted to have a gay old time.

I'll take a break from being mean on the movie to say that all the men are cute in it.

As we go through the movie, we actually get a fairly honest and eye-opening look at how supposedly open-minded people regarded gay rights. Charles and Amy both make plenty of mentions about how they “don’t care what people do behind closed doors” or being open to gay people. Still, they treat Oscar’s (mistaken) sexuality as something exotic or different, which ends up othering him. Meanwhile, when Oscar’s sexuality makes it on to the front page of a major Chicago newspaper (I guess that was news back then), his parents are shocked. While his Mom tells Oscar that she still loves him, his Dad breaks things in rage and is half in tears. His Dad’s anger is treated as a punchline, with Oscar being the butt of it. The joke relies on the understanding that no Father would actually want a gay son, with Oscar being the butt of the joke. 

Peter Steinberg: Oskie, I'm a professional. I went to graduate school. I did all-nighters my senior year. I did a semester in Egypt. Do you have any idea what toilet paper feels like in Egypt? I delivered cinnamon rolls on a truck with bad suspension for three years! Do you know what that does to your kidneys? My poor kidneys! My freaking kidneys! My poor freaking kidneys! My freaking, scarred, bruised kidneys! 

Yes, Peter is not one of the titular three in Three to Tango, but it still is a bit baffling how sidelined he becomes as the stakes get higher and higher. The final set-piece is at the Lesbian and Gay Professional Award Show, where Oscar is being honored as the “Gay Man of the Year.” It’s utterly homophobic to snub a gay man at any awards show, no matter how small. Award shows are what we live for. Jokes aside, the movie never really gives him much of an interior life, but it does set up that he spent his entire life trying to achieve this new level of professional success. He and Oscar may get the job in the end, but we barely get his reaction to achieving this success. All the movie is interested in is rewarding Oscar with his manic pixie dream girl, Amy.

Then again, we do see Amy’s newly out ex-boyfriend, Kevin Cartwright (Cyle Cozart), approach him at the final party. Here’s hoping Kevin and Peter made passionate love that night and in the morning bitched about the crazy straight people in their life.

To be fair, I had an absolute blast with my Three to Tango pairing - me, this movie and a bottle of wine. Comedy is tragedy plus time. This movie is tragic, and enough time has passed that it’s incredibly fun to laugh at. The gay best friend continues to this day, with just as many lazy examples as thoughtful ones. Yet, we haven’t seen a swing and a miss quite as wild and laughably off-base as Three to Tango in a while. That’s something worth celebrating… I guess.

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

• Bernstein (Antonio Fargas) in Next Stop, Greenwich Village (1976)

• Erich (Norbert Weisser) in Midnight Express (1978)

• Toddy (Robert Preston) & Squash (Alex Karras)  in Victor/Victoria (1982)

• Dolly Pelliker (Cher) in Silkwood (1983)

• Buddy (Charles Grodin) in The Woman in Red (1984)

1990s and the 2000s

• Tim (Nathan Lane) in Frankie & Johnny (1991)

• Hedra Carlson (Jennifer Jason Leigh) and Graham Knox (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)

• Christian (Justin Walker) in Clueless (1995)

• Jane (Whoopi Goldberg) in Boys on the Side (1995)

• Sterling (Patrick Stewart) in Jeffrey (1995)

• Cleo (Queen Latifah) in Set It Off (1996)

• George Downs (Rupert Everett) in My Best Friend’s Wedding (1997)

• Simon Bishop (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)

• Stanford Blatch (Wilie Garson) in Sex and the City (1998 - 2010)

• Michael (Stuart Wells) in Billy Elliot (2000)

• Robert (Rupert Everett) in The Next Best Thing (2000)

• Buck (Mike White) in Chuck & Buck (2000)

• Patti (Sandra Oh) in Under the Tuscan Sun (2003)

• Michael (Robin de Jesús) in Camp (2003)

• Damian (Daniel Franzese) in Mean Girls (2004)

• Todd (Keir O’Donnell) in Wedding Crashers (2005)

• 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)

The Now

• Patrick (Ezra Miller) in The Perks of Being a Wallflower (2012)

• Matt (Matthew Wilkas) in "Gayby" (2012)

• Abby Gerhard (Sarah Paulson) in Carol (2015)

• Duncan (Pete Davidson) in Set It Up (2018)

• Oliver T'Sien (Nico Santos) in Crazy Rich Asians (2018)

• Jack Hock (Richard E. Grant) in Can You Ever Forgive Me (2018)

• Artie (John McCrea) in Cruella (2021) and other “First Disney LGBTQ+ Characters (2013-2021)

Who is your favorite (or least favorite) example of a “gay best friend” in movies? Let us know in the comments below.

Comments

[Amy Camus]

Ummm... That's Dylan McDermott, not Dermot Mulroney

[James from Ames]

https://www.youtube.com/watch?v=XGqSn5Cnw74

[Sarah]

The Friends cast really did make a lot of terrible movies didn't they? And I somehow ended up watching most of them. This movie is terrible but I totally get what you mean about it being a captivating hate-watch. Also why were we so obsessed with architects in the 90s? I know this has nothing to do with the article but seriously so many male protagonists in 90s movies were architects. It was such a bizarre trend.

[Joe G.]

I'm pretty sure I've memory holed all the bad films Matthew Perry starred in during his Friends run. What's so odd about so many of these types of films, is that they essentially asked the actors to play their friends characters - something we could watch about 44 weeks during the year. The most successful and interesting moments were when they didn't (e.g., Scream, The Good Girl, The Opposite of Sex).

This film seems very of its time in the worst of ways. I do appreciate you highlighting the few moments where the film gets complex about homophobia and masculinity. However, It also seems wildly homophobic to cast Dylan McDermott as a straight guy here.

[davidandwaffles]

It makes sense that Perry would think such a moronic premise would work.
Half of the punchlines on Friends were some variation of gay panic, mistaken gay identity or just saying the word "lesbian" to rapturous reception from the studio audience.