First Time Watch: Three to Tango (1999)


By Christian DiMartino

Three to Tango is very much a one-joke comedy. It’s a joke that could have been funny, and similar scenarios have been funny in movies like Tootsie and Mrs. Doubtfire. Since Three to Tango is from the late 90’s though, its jokes feel stale, outdated, and mostly rely on stereotypes.

Three to Tango has a significantly different scenario than Tootsie and Mrs. Doubtfire, but those films are mentioned here because both films, like this one, revolve around a guy who must keep up with a lie that he has gotten himself into. With the earlier two films, the stakes felt high, and there was a pretty good understanding for why the characters had to keep up the facade. With Three to Tango, just about every character, outside of Matthew Perry’s, is an idiot who won’t listen. It’s not that he doesn’t try to get his voice out there, but rather, he doesn’t keep trying, and his lie is far less significant than, say, disguising yourself as a woman.

Perry plays Oscar, who with his business partner, Peter (Oliver Platt) are trying to get funding for some big project from a successful businessman, Charles (Dylan McDermott). For whatever reason, the plot is set in motion whenever Charles’ assistant overhears a conversation between Oscar and his partner, making them sound like they’re gay. It doesn’t help whenever rival gay business partners (John C. McGinley and Bob Balaban) spread gay rumors about them, nor does it help whenever Oscar is seen kissing Peter’s forehead repeatedly after they get their big break.

Under the assumption that Oscar is gay, Charles asks Oscar to spy on his mistress, Amy (Neve Campbell), who he has suspicions of. Not knowing why he was chosen specifically, but afraid of declining in the event they lose the project, Oscar agrees. He soon meets Amy, and their first encounter isn’t romantic in the slightest… but it’s love? I guess? Basically they fall for each other because the screenplay requires them to, but Amy lowers her interest after she discovers Oscar is gay. It is soon brought to Oscar’s attention that he is gay (though he isn’t), in a scene that comes a little too early into the movie, and even then it wouldn’t have been funny: upon hearing the news, he runs down the streets of Chinatown screaming, and chickens jump out at him. Of course. I say this scene comes too early because at this point of the plot, only two people think he’s gay. Knowing he is in a bind, Oscar continues the charade because he doesn’t want to lose the project, nor does he want to upset Amy, and soon he becomes a town hero for being gay. Again, this was the 90’s.

Matthew Perry and Neve Campbell were the draw here. One could hope that Perry, who hasn’t done a project in years, is doing well. Campbell has aged like a fine wine, but she doesn’t do a whole lot anymore, so you take what you can get. Even if it’s this. Their relationship isn’t very convincing, nor is the big speech he delivers towards the end. Here is a romantic comedy in which we know the outcome (how often do we not though?), and so we just watch the wheels spin until we reach it.

The movie is undeniably amusing, and Perry, being the charmer that he is, does his best to keep the material afloat. The material is the problem though. Take a scene in which the whole city discovers Oscar is gay. One of his friends drops a radio while he’s in the bathtub, and a bunch of other over-the-top, unfunny reactions ensue. Following this scene is the moment that made my eyes roll the most: Perry’s outing makes the front paper, and while aboard a bus, a gay man locks eyes with him, and soon starts eyeballing Perry from the front, and the back. Platt’s character also has similar moments.

Guys, let me state for the record that we are not all like this. This film delivers cartoonishly gay characters that you’d expect to see in, well, a 90’s comedy. Was it a different time? Well, yeah. However, it probably wasn’t funny then, and in 2020, in which there aren’t many laughs to be had in the first place, it isn’t funny now.

Note: This is not an actual flaw, but Matthew Perry’s hair really bothered me in this movie. 

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