7 Best Funny Movies On SHOWTIME

1. The Disaster Artist, 2017

A hilarious and smart comedy that is almost impossible to hate. It doesn’t matter if you liked The Room or not; or if you’ve even heard of it, you will find The Disaster Artist extremely enjoyable. Same applies for James Franco, it’s irrelevant if you think he’s the hottest man walking or a complete waste of screen-time - this movie is better approached without any preconceived ideas. It follows the true events surrounding Tommy Wiseau’s making of The Room, a movie so bad it actually became a worldwide hit. Tommy’s character, played by Franco, is 100% mystery. He pops out of nowhere and does and says things that contain little to no logic. Capitalizing on this, the movie is both absolutely hilarious and intriguing from beginning to end.

2. Work in Progress, 2021

This underrated, semi-autobiographical series follows Abby (Abby McEnany), a queer person struggling with OCD and depression. She navigates life's ups and downs with humor that is both offbeat and sympathetic, but things quickly take a turn for the romantic when Abby's sister sets her up with Chris, a trans man 20 years her junior.

Relatable, hilarious, and frank, the miniseries is a tender gem of a show. It's also effortlessly relevant, which checks out: creator and star Abby McEnany mines inspiration from her own experience as a queer artist, while executive producer Lilly Wachowski (The Matrix) reportedly made a big push for authentic trans representation.

3. The Watermelon Woman, 1996

This drama was the first feature written and directed by an out Black lesbian, Cheryl Dunye, and it is an absolute joy: a cheeky faux-documentary that ingeniously blends lesbian dating life with a historical dive into Black actors in 30s Hollywood.

Dunye plays Cheryl, a self-effacing version of herself, an aspiring director working at a video store who begins to research an actress known as the Watermelon Woman for a documentary. The more Cheryl dives into her research, the more she sees parallels between her subject and her own relationship.

As incisive as it is funny, The Watermelon Woman shares some common ground with other major indie debuts of the era like Spike Lee’s She’s Gotta Have It and funnily enough Kevin Smith’s Clerks, but Dunye’s style is wholly her own and a dazzling treat to experience.

4. Swiss Army Man, 2016

Probably the weirdest film you'll ever see. Paul Dano plays a borderline suicidal man who befriends a farting corpse that washed up from the sea as played by Daniel Radcliffe. It's an adventurous, witty and hilarious film yet it is filled with discreet and very deep lessons about society and norms. The soundtrack is so charmingly unique as well, it's a definite must-watch for anyone looking for a refreshing comedy.

5. Back to Life, 2019

Daisy Haggard plays Miri, a girl who just got out of an 18-year prison sentence for a crime she committed in her teens. And what an important 18 years she missed: so many technological developments - and actually much of her own development-, plus, shocker, it looks like her boyfriend from back then did not wait around for her.

But Miri's biggest problem is that the town hates her guts. So the show is her navigating all of that while trying to get a job and put her life on track. It's an endearing comedy about fighting for normalcy when nothing seems to be going your way.

6. Up in the Air, 2009

Ryan Bingham (George Clooney) is a corporate axman, he comes in a fires people when the managers are too afraid to do it themselves. The nature of his work requires a lot of flying, short lived meetings in transit zones and he absolutely loves it, and he has a certain goal in mind. When the company tries a new approach to corporate downsizing he has to change his way and view of life. It's full of cynicism and warmth. If you are familiar with Jason Reitman's previous work, you'll feel right at home, if you don't : Get to it!

7. The Guest, 2014

This is a fun genre mashup B-movie, in the vein of old John Carpenter films or those movies you used to run across on late-night cable in the 80s and early 90s. Dan Stevens (that handsome chap from Downton Abbey) gives a knock-out performance as the titular guest (David), who in the movie’s beginning has just shown up on the doorstep of the Peterson family. He says he’s there to pay his respects to the family -- he served with their son, who died in action -- but there is something just a little bit off about him. Everyone in the family is charmed by David except for daughter Anna (Maika Monroe), who approaches him with extreme caution even though she’s clearly impressed by his six-pack abs. The films starts at a slow burn before devolving into nutty, violent chaos, but maintains a dark cheeky sense of humor throughout. The goth pop soundtrack is also killer.