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Overrated, Underrated, or Properly Rated: The ‘Classic’ Films of Matthew Perry

Were Matthew Perry’s starring vehicles really that bad? Yes, for the most part, they were.

Matthew Perry is missing a chunk of his right middle finger. Feel free to open a new tab and Google it. It’s true. The tip of his finger was sliced off by a slamming door when he was a child. I don’t know if it’s because the directors and cinematographers who shot Friends did such a stellar job hiding it or if the tiny tube TVs and grainy analogue picture quality of the era didn’t lend themselves to the sort of obsessive analyzing of every frame of every piece of filmed entertainment ever made that we engage in now, but I never noticed until two days ago. Now, any time I see Perry, I look for that finger. I am compelled by forces I cannot hope to understand, my eyes drifting downward in order to catch a quick glimpse or just to see how he tries to hide it in a scene.

Getting a piece of your body lopped off was just one of many challenges faced by the former Chandler Bing, but other than the ever-increasing bags under his eyes, it’s the most outward expression of the toll life has taken on him. To many, he’ll always be seen as a “TV actor,” unfit for the privilege of having your face blown up to mythic proportions on a big screen. Believe it or not, there was a time when acting on TV was seen as a step down rather than a respite from the cacophony of big-budget blockbuster filmmaking.

After the runaway success of Friends, it was only natural for the cast to attempt to make the leap to features during the summer break. Between 1994 and 1997, each of the Friends stars tried on the movie-star label to varying results. Jennifer Aniston did She’s the One and Picture Perfect. Matt LeBlanc starred in Ed, a film where a chimp plays baseball, ruining the natural order of the universe. Courteney Cox played the love interest in Ace Ventura: Pet Detective and the ambitious TV reporter in Scream. Lisa Kudrow hit with Romy and Michelle’s High School Reunion. David Schwimmer toplined the Matt Reeves/J.J. Abrams indie joint The Pallbearer1 with Gwyneth Paltrow.


Considering the pedigree of the cast and crew involved, The Pallbearer deserves a second look, but that’s a story for another day.

Each of those films played to the strengths of its stars. Aniston did the classic rom-com thing she was put on this earth for. Scream allowed Cox to be sarcastic but charming. Romy and Michelle let Kudrow be dim-witted yet endearing. Schwimmer got to be neurotic. LeBlanc hung out with a monkey for three months. Even though some of these films failed at the box office, they were at least on brand for the actors and weren’t career killers.2 That cannot be said for Perry. Despite having most of the best lines week in and week out on Friends, it’s fair to say he’s neck and neck with Schwimmer for the worst post-show career of that cast. Like a top college prospect who gets drafted in the first round but is out of the NBA after three years, Perry never truly broke through in the cinema. What we remember of his movie work is his relentless mugging and flitting from job to job with no rhyme or reason. Can you pinpoint what defines a Matthew Perry movie? Can you even name a Matthew Perry movie?


Ed might have bombed, but LeBlanc still got to do Lost in Space in 1998, which would have been the movie to launch him to the next level if it wasn’t horrible.

With his fourth attempt at a TV comeback, The Odd Couple, premiering tomorrow, I made the harrowing decision to rewatch all the films where he was the lead in an effort to figure out what went wrong.


Fools Rush In (1997)

I embarked on this journey with my eyes wide open. No one forced me to watch these films. I did this of my own free will. I was not a hostage. No one was holding a gun to my head. I chose this.

First up is Fools Rush In, a light trifle about a cross-cultural marriage between a nebbishy WASP from Manhattan and a free-spirited Mexican American from Las Vegas. Instead of a juicy batting practice fastball, Perry’s first lead role was a Mariano Rivera cutter — close to what you expect until the very last minute.

Perry trades in the sarcasm and cynicism of Chandler for a heaping helping of lukewarm oatmeal. He plays a giant wiener with no redeeming qualities besides being Matthew Perry. When our boy finds out his one-night stand is pregnant, his first move is to not-so-subtly suggest she get an abortion. Later on, he berates her in public for not supporting his career as a … nightclub designer? Is that a real job or did the ’90s just make that up? Salma Hayek’s character doesn’t get off that easy either, as she pulls the classic “second-act fake abortion” move to get her husband to break up with her.

Any of this sound hilarious yet? Did I forget to mention all the jokes about how Perry’s character is from New York and wears ties, but his hot new wife is crazy and speaks Spanish all the time? Her family is stereotypically “hot-blooded” and passionate while his family is hilariously emotionally stunted and racist! How about the scene in which Perry creepily kisses his wife’s pregnant belly before defiling her sexually? If you ignore that this is supposed to be a comedy, it kind of works. If, for some unknown reason, you choose to watch this movie, pretend that it’s a Crash-esque melodrama about white privilege. A few of the heavy scenes between Perry and Hayek really hit you in the gut, and I found myself rooting for them to work it out. Just don’t expect to be amused. UNDERRATED

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Almost Heroes (1998)

Fools Rush In is a competently made but unfunny piece of work. I walked away from my TV feeling cheerily ambivalent about the movie. Almost Heroes, on the other hand, is a spectacular train wreck that will rob you of your life force. It’ll suck your brains out through your eyeballs, stretch out all the collars on your sweaters, then have sex with your mom. No, that image doesn’t make sense to me either, but it’s the only way to describe this movie. Perry plays a foppish dandy with a shitty accent and Chris Farley portrays Chris Farley, in a historical farce about a pair of imbeciles trying to beat Lewis and Clark to the Pacific Ocean. The movie, ineptly directed by Christopher Guest, is like 90 minutes of BDSM ball torture followed by Chris Christie rubbing his salty undies in your face. It looks like it was shot on Tom Sawyer Island and that someone put plastic wrap on the lens. The music and the opening credits are so bad that you have to wonder if the studio took its money away during postproduction because it knew how bad the movie was. This was Farley’s last film before he died, and on the continuum of shitty last films, this sits somewhere between Street Fighter and Queen of the Damned, about as far away from The Crow and Giant as possible. When this movie came out, it was ignored by most and loathed by everyone else. It still sucks. PROPERLY RATED

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Three to Tango (1999)

After Almost Heroes, I was dying for a reprieve, but in Three to Tango, there was no quarter for me. There’s something about Perry starring in films with a shameless bait-and-switch opening. Fools Rush In starts with a series of shots of New York at Christmas, so you think, Oh, this is a Christmas movie. Let’s settle in for a feel-good holiday adventure. Ten minutes later, the movie is taking you to Las Vegas and throwing abortions and casual racism at you. Not what I signed up for, guys. Three to Tango pulls a similar move with a stylized opening credits sequence featuring swing dancers. Oh, a movie about swing dancing. How fun! Wait, did I see Patrick Van Horn, the O.C. dickhead from Swingers in the opening credits? This is definitely about swing music!

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There is no swing dancing in this movie (but there is the above scene in which Dylan McDermott wears a VR headset!). It is not about swing music. It’s actually about an architect who everyone thinks is gay and how that ruins his life. It does have a swing music score and an inexplicable swing music video that plays over the credits. I could not close my mouth for the entire length of the music video, because I was so shocked at how brazen, shameless, and moronic the cultural bandwagoning was. I hear the kiddies love swing music or something. Maybe if we, like, put a bunch of it in our lazy, borderline offensive gay panic rom-com, they’ll tell their friends how “cool” our movie is!

In a clever attempt to distance himself from his iconic role, Perry dyed his hair some sort of rust color that makes him look like Corky St. Clair. Of course, while the intention was to make the audience forget that he was the “guy from TV,” just like his poor middle finger, the more you try to hide it, the more attention you draw to it. Overall, this is a bad hair movie. Case in point, all-star character actor Oliver Platt, who plays Perry’s actually gay sidekick:

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It’s like the Venom symbiote is growing on his head. He looks like fat Peter Dinklage wearing a suit from Rochester Big & Tall. His sideburns are dangerously close to consuming his entire body, and no one is doing anything to stop it. What is happening here? This movie is bad, bad, bad. It ends with Perry revealing how not-gay he is to a room full of gay people who inexplicably cheer for his brave admission that he is, in fact, a heterosexual male who just wants to have sex with Neve Campbell. This is a movie in which Perry literally runs through the street screaming because people thought he was gay.

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Our man is so upset, you’d think he’d just watched Almost Heroes. PROPERLY RATED

The Whole Nine Yards (2000)

Has anyone ever uttered the words, “I’m so glad The Whole Nine Yards is on”? I was so fucking thrilled when I got to this point, because I remembered really liking this movie when I was 16.3 It did not disappoint. Granted, we’re not talking about high art, but it’s well staged, makes great use of picturesque Montreal, and has a couple of fun supporting performances from Amanda Peet and Rosanna Arquette, harmless scene-chewing by Kevin Pollak, and, most importantly, Perry’s finest performance in a movie. I don’t know if it was the pressure of acting next to real-deal movie star Bruce Willis, the novelty of finally having a halfway decent script, or something more metaphysical, but Perry rose to the occasion and worked perfectly here.


And not just for the female nudity.

My theory is simply that Perry is always at his best when the story beats and the performances around him are constantly ratcheting up the tension. As an actor, he needs the screws put to him, because he’s funniest not when he’s being smarmy or charming, but rather when he is being abused mercilessly. For some primal reason4 I just love watching Perry get cuckolded, bullied, and threatened with physical violence. When he’s placed in believable, menacing mortal danger, the comedy works. There’s just enough legit tension for The Whole Nine Yards to make use of Perry’s masochistic skill set. From his breakdown in the car through to the cathartic finale, Perry’s Oz is batted around like a volleyball and I thoroughly enjoy every second of it.


Probably due to his soft jawline.

Contrast this film with something like Almost Heroes, where the tone is so broad that you can’t buy in to the stakes enough, or Fools Rush In, where the proceedings are so hopelessly earnest that no actual comedy can flourish. This is a fun, clever movie where a filmmaker finally figured out how to use Perry. In the context of the rest of his CV, The Whole Nine Yards deserves way more credit for actually getting great work out of the poor bastard. UNDERRATED

Serving Sara (2002)

Two steps forward, 500 steps back. I feel like I was walking around without a care in the world, footloose and fancy free, and then stepped in a big pile of cow shit that I didn’t see coming (but should have). Serving Sara, directed by Reginald Hudlin, is like Midnight Run mixed with hitting yourself in the head with a shovel, which is how I imagined it was pitched to the studio. Perry plays a process server who is tasked with serving divorce papers to the titular Sara, played by Elizabeth Hurley.5 The “fun” little twist of the plot is that Sara gets him to serve her husband instead, in exchange for a share of her divorce settlement. For yet another interminable 99 minutes, Perry and Hurley race around Texas trying to find her husband, gamely brought to life by Bruce Campbell. Because Campbell’s character made a fortune as a rancher, there’s a plethora of cow-related gags. Cow patties are stepped on, naturally. Perry has to stimulate the prostate of a bull in order to get it to ejaculate inside a sperm receptacle shaped like a cow. This was the second instance of animal sex in a Perry movie, as Almost Heroes featured a scene in which Farley becomes aroused while watching two pigs copulate in a barn. Really. No, really.


I’ll give the movie this: Hurley was an inspired choice, since Perry is sort of like the American Hugh Grant.

Yet again, Perry tried on a different cinematic persona — this time, he’s doing a low-rent Fletch era Chevy Chase. Instead of giving us the underdog we want, he demands we think he’s cool. He wears a leather jacket and some “edgy” stubble through the whole movie just to hammer home the point. Quit trying to fool us, Matthew Perry! We know you’re not cool, man. Get out of the way of yourself!

I could tell you to watch this for the morbid curiosity factor or because it’s one of the earliest movie roles of Amy Adams, but I won’t. Look, this shit sucks. Everyone knows it. PROPERLY RATED

Screen Shot 2015-02-18 at 12.08.00 PMWarner Bros.

The Whole Ten Yards (2004)

This is the end. The final sequence. The Stargate from 2001. I am about to evolve into a Star Baby. One month before the final episode of Friends aired, Perry returned to the comforting bosom of the best film role he ever had. It makes perfect sense if you ignore the end result. If you’re Matthew Perry in 2003-04, you’re out of rehab. You’re clean and ready to work. Your gravy train sitcom is ending. In your last film, you stuck your arm in a bull’s ass. You need a hit. Why not a sequel? Well, because doing a sequel to a very modest hit four years after its release despite the ending of said film not exactly screaming out for a sequel is just a dumb idea. It’s just dumb. As directed by legendary studio comedy cheesemonger Howard Deutch, all the menace and real danger from the first film was replaced by a double helping of Pollack in old age make-up acting as though he is in a movie by himself. Willis had already started his “Keep Getting Them Checks” farewell tour of sequels, direct-to-video turds, and quickie cameos in G.I. Joe and Expendables films. With a substandard, retread script and no one to play off of, Perry sinks further into oblivion. PROPERLY RATED

Bad career decisions combined with personal demons hobbled what could have been (and might yet still be) a fruitful movie career. The man can act. He nails the black comedy of The Whole Nine Yards and elevates the drama in Fools Rush In. Maybe this is me rooting for the underdog again, but I would love for The Odd Couple to be good and for Perry to enjoy a career renaissance. But, based on this experiment, I’m not holding my breath.