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Best Comedy Movies on Plex

The romantic poet Lord Byron once quipped “always laugh when you can, it is cheap medicine” and my god is it high time for a laugh. People are stuck in their homes, rationing toilet paper and watching their teens dance on TikTok. We’re like three Tina Turner sing-strides away from Thunderdome (will speargun for flour @me) and so what better time to laugh it up?

This month we’ll explore five comedies you can watch for free on Plex, and hopefully, the laughter will provide a period of blissful retreat from the malaise of cabin fever around us all.

1. She’s Out Of My League

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We usually do fairy tales with the handsome prince saving the poor peasant girl, but the reversal in this film is a welcome change. She’s Out Of My League is what happens when a stunning, self-made woman falls for a TSA worker, and the various complications involved in such a pairing. In one way, it’s a love letter to the city of Pittsburgh, which is vastly underrated. In another way it’s an investigation about ingrained class warfare and how we’re often our own worst critic.

But honestly, the movie is too busy bringing the funny to even tip its hat to those themes. It’s a fairly down-the-middle romantic comedy that does a solid job of toeing the line between witty and smutty. Jay Baruchel plays the lead and I kept hoping for him to rise above the preconceived pigeonholing of his looks and his vocation to be the type of man who could justify Cinderella coming to woo him, but I’m not sure he ever really rose to the occasion. Still, the supporting cast is sharp and funny, and Alice Eve is so beautiful it’s kind of unfair. Come for her loveliness and stay for the inspired snark of Krysten Ritter.

Watching her spar with T.J. Miller was worth the price of admission.

Also, I love the actor Nate Torrence, seen below on the right playing the role of Devon. Seeing him on screen just makes me happy. Look at that mug. What a beaut.

The movie is fun, and while the language may be a tad rough for some viewers, mostly you have an easy, by-the-numbers romantic comedy where you’ll laugh at the wacky ancillary players and root like crazy for the two leads.

2. Drinking Buddies

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“Yeah, but if I introduce you, will you not be a dickhead and not call me names and don’t say anything stupid or mean and don’t like punch me in the face?”

Drinking Buddies is less a destination than a journey. Directed by Joe Swanberg, it’s part of the mumblecore world of films: basically a long improv sketch. Swanberg introduced the actors to the premise, gave them a few guidelines, and rolled cameras four days later. Just writing that makes my stomach tighten up, but because of the chemistry of the talented leads, the results were pretty impressive.

Jake Johnson leads a cast of Olivia Wilde, Ron Livingston and Anna Kendrick with an assist from Jason Sudeikis. It’s generally a story about two brewery workers with a special connection and a glimpse at the people they’re dating. But this is certainly one where your mileage may vary. Some people love the authenticity of the world, others have trouble waiting for more scripted plot points to happen. I found the subtle commentary on functional alcoholism interesting and it reminded me of the type of relationship angst I was glad to grow past.

Now, I have to admit, I’m a little biased because I’ve had a moderate crush on Olivia Wilde since seeing her in a tiny role in 2004’s The Girl Next Door.

And I’m a huge, huge Jake Johnson fan from his work on New Girl and Stumptown and basically everything he does. I can’t get enough of the guy. He’s great in everything. Except this picture where his feet are filthy because I kind of have a feet aversion. Dude has some deep-ass arches. But in general, every role he touches he turns to gold.

It’s also kind of interesting to see how many people have migrated from Team Kendrick to Team Wilde over the years. (If you haven’t seen Olivia Wilde’s Booksmart, by the way, do so tout suite). But that said, this is a polarizing film. I was very open to it and it worked, but I have co-workers who loathe this movie and will drunk-yell about it all night if you give them enough Hefeweizen. (Which I often did before an invisible pathogen shut down the human race).

If you’re able to just relax and let Drinking Buddies come to you in its disarming sort of way, you have a chance to be really charmed by it.

3. Wonder Boys

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“Trust me, James, when the family pet’s been assassinated, the owner doesn’t want to hear one of her students was the trigger man.”

Wonder Boys is just about as close as you can get to a film feeling like a novel. It’s the one movie that makes me simultaneously feel both old and young. We open in a creative writing seminar, migrate through a rainy car ride and land in an academic cocktail party on a snowy night in Pittsburgh. You can almost smell the tweed when you start watching.

And then you smell the weed.

Starring Michael Douglas as an emotionally dispirited professor, we follow him down a liberal arts rabbit hole as he loses a wife and gets caught up in a series of bizarro events that still manage to maintain a put-upon literary quality.

The rest of the cast is stellar. Frances McDormand, Tobey Maguire, Robert Downey Jr., Katie Holmes and Rip Torn bring the script to life, and capture the most heartfelt moments of the Michael Chabon novel upon which it’s based. McDormand is so amazing in this that it hurts my bones to watch. She’s a living legend.

Wonder Boys is a jewel in the directing crown of the late Curtis Hanson, one of Douglas’s best performances, and Downey Jr.’s before he was Iron Man. In fact, without this role, and his later one in 2005’s Kiss Kiss Bang Bang, I’d posit that there never would have been a Tony Stark in his future. And lest you misunderstand me, Wonder Boys isn’t your grandpappy’s literary movie. Guns, dogs, sex, unexpected babies, cops, drugs, infidelity, stolen cars and of course, Marilyn Monroe all vie for screen time in this deeply moving, relatively unheralded masterpiece. I adore this movie. Hard stop.

4. Big Night

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“A guy works all day, he don’t want to look at his plate and ask, “What the f*** is this?” He wants to look at his plate, see a steak, and say “I like steak!”

Big Night is like being hungry and then gorging yourself with your favorite food. It doesn’t just fill the hole, it feeds the soul.

It’s a relatively small story: Despite having a virtuoso chef, an Italian restaurant is facing foreclosure and must plan one hail Mary dinner to save it all. But inside of that premise, the language crackles. A combination of outstanding writing, note-perfect acting and masterful directing, Big Night takes you back to the Jersey Shore before gym, tan & laundry. The 1950s, when the sky was the limit and the American dream lured people from every nation in the world to make it big. The cast, itself, is kind of jaw-dropping:

But the relationships? The stress and the passion? The music! The dancing! It’s all wrapped up into a little package sure to be adored by foodies, but accessible to anyone who’s had to navigate the landmines of a tight-knit family. As much drama as it is comedy, I put it here because it’s honest and powerful and the small moments make me laugh out loud.

5. Clue

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There are only two groups of people in the Clueniverse: people who understand that Clue is one of the greatest comedies ever made, and people who don’t yet realize that. Unlike many titles from the 1980s, Clue is timeless. A Whodunit for the ages. The jokes are evergreen and the comedic timing is spot on.

If you like physical comedy, Clue is your Huckleberry. Clue giveth and Clue taketh away, often in the same scene. In addition, it features multiple endings, which was a daunting undertaking in the 1980s but is now a delight that wraps up the film with a nice bow. A legendary ensemble cast, a shrewd script and lightning-fast repartee make Clue a revelation that never gets old and never disappoints. I’ve watched it probably fifty times and I still laugh like an insane person on meth every time I see it.

Did any of these comedies tickle your funny bone?  Wade into the comments to let us know which one was your favorite!

Written By

Thor is the Editor-in-Chief of The Gist and a father of four. He's a lover of ancient history, Greek food and sports. He misses traveling and thinks that if libraries were the center of American society, many things would improve overnight. You can hit him up at [email protected].

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