100 Best Grown-Up Comedy Films

Surprisingly heartwarming and enjoyable, The Unbearable Weight of Massive Talent turns its over-the-top premise into a tribute to the one and only Nicolas Cage. Playing an unfulfilled and broke version of himself, Cage’s next gig is an appearance at eccentric billionaire Javi Gutierrez’s (Pedro Pascal) birthday party. They strike up an instant bond over their love of film. However, the CIA suspects Gutierrez’s involvement in a political kidnapping, forcing Cage to investigate his friend. The film brilliantly employs those 90s-esque action tropes that Cage’s movies are known for – the car chases, the sunglasses, and the eccentric characters. Cage himself fully commits to the premise, but Pedro Pascal adeptly matches his energy with his easy-going charm. Their moments together and their shared love for cinema makes this a great watch.

Before he was Jim Morrison, Iceman, or Batman, Val Kilmer made his big screen debut as Nick Rivers, the doltish American rock ‘n’ roll idol who is unwittingly embroiled in an East German underground resistance plot in Top Secret!. Skewering everything from WWII romances and Cold War spy thrillers to ‘60s popstar musicals, this delightfully silly spoof from the team behind Airplane! is jampacked with sight gags, double entendres, and multi-layered setpieces delivered at such a manic pace that you’ll need several rewatches to exhaust all of its comedy. Its lowbrow style means that some jokes are undoubtedly dated, but there’s a lot of timeless wit on display here, including zinging one-liners, tongue-in-cheek lampooning of cinematic clichés, and slapstick gags in the vein of masters of the form like Jacques Tati and Buster Keaton. Top Secret! is blessedly under no illusions as to what we want from a movie like this, so the fact that there’s no comprehensible plot in sight only adds to the enjoyment here.

It’s always tricky translating literature to screen. In Shortcomings’ case, it struggles to make its Berkeley and New York settings appear more lived-in than just a few postcard-like frames. You could also tell that the conversations it stirs up about things like representation and mixed-race relationships began in the early aughts, when the novel it was adapted from was first released. But those lapses are small and forgivable in the face of a lovely ensemble cast and a whipsmart script.

It also takes a special kind of skill to make a character as fiercely unlikeable as Ben (Min) watchable, to hold up a mirror to the audience and make them stay. Thankfully, it’s a skill that Tomine and first-time director Randall Park display with such grace. Ben, Alice (Sherry Cola), and Miko (Ally Maki) are flawed and often pathetic, but they’re also honest reflections of who we become when the demands of self-preservation and romantic openness clash. It’s a little unnerving to hear them verbalize what we’ve always feared about ourselves, but it’s also exhilarating, not to mention comforting, knowing that we’re not alone in feeling this way. Shortcomings works because it doesn’t confine itself to genre: it’s a character study first, and a romantic comedy second.

When falling in love with another, or when another person falls in love with you, the relationship is formed by the ideas in your and their heads, specifically about your dynamic, your respective personalities, and the potential outcome of this love. Law of Desire is centered on this idea, unfolding through a chaotic gay love triangle that demonstrates the ways the ideas and fantasies can differ. And as the characters inevitably go through fairly melodramatic reactions when they realize the desires of another person, in the most colorful fashion (literally and figuratively), Pedro Almodóvar creates an amusing and daring examination of the genre it’s inspired by.

Starring Ryan Gosling, Emily Mortimer, Paul Schneider, Kelli Garner and Patricia Clarkson. Lars and the Real Girl is a funny and thought-provoking look at the psychology of loneliness and the healing power of love. I rented this a few years back because of Ryan Gosling – he had just blown me away in Fracture so I was trying to catch up on his other movies. It was an unexpected gem. One of the sweetest movies I have ever seen – it was kind of like a fairy tale. With a blow-up doll. Yes, that’s right.

After being held captive his whole life, a man sets out to finish the only show he’s ever seen. Thoughtfully written with a creative cast; it is not a film you would expect to laugh at and enjoy so thoroughly with such an unconventionally dark premise. However, it is a hilarious, wholesome, and loving film that will leave your heart feeling warm.

In this office comedy of errors, Javier Bardem plays Blanco, the titular boss, but whether he is actually good is what the movie wryly examines.

As head of a small manufacturing company, Blanco treats his employees intimately, going so far as make their problems his own. He believes this is why his company is nominated for an excellence certification, but as he waits for the possible award, cracks start to appear in his “work is family” facade as everything that could go wrong, starts going wrong. The Good Boss is an anxiety fest for Blanco to be sure, but a winning tragicomedy for us all.

Rye Lane knows it’s treading familiar ground by having its charming leads fall in love as they walk and talk their way through a beautiful city. So instead of experimenting on a tried-and-tested setup, it smartly focuses on specificity. It hones in on the characters’ Gen Z woes and cranks up the British references, giving itself character and charm for days. It also finds other ways to be inventive as it trades plot twists for bold editing and camerawork. Rye Lane is a refreshing entry into romcom cinema, but it is also obviously a big fan of it as it holds plenty of homages and subversions of the genre. This one is made for and by romcom fans, and it’s always nice to see a modern love story set during our times.

True to its name, Joy Ride is a raucous delight that has everything you want out of a road trip comedy and more. There’s love, sex, adventure, and even music, but most of all there’s friendship, the interesting complexities of which are explored against the backdrop of race. There’s something meaningful keeping everything together at the core, and first-time director Adele Lim—helped by a strong script and cast—does an excellent job of holding it down. The film is also just plain funny. There are physical gags and of-the-moment jokes, plus a couple of insider quips made for and by the Asian community. But apart from the hilarity and tenderness, the film also delivers in the visual department: it looks gorgeous, not only because the characters are tourists who embark on a jet-setting adventure, but because of the inspired animation and vibrant editing. 

If Pete Holmes’s new stand-up special comes off more like the comedian just trying out a bunch of random material instead of communicating coherent, overarching ideas, his writing is so strong that it hardly matters. You can tell Holmes is an incredibly confident performer in the way he deploys a wide range of techniques to get his jokes across: exaggerated voices, feeding off of the audience, even messing up his own jokes and rolling with the punches. But his turns of phrase are really the stars of the show here, as he gives even the most ridiculous anecdote a sense of imagination and unique visual texture. This is classic (if somewhat unsurprising) stand-up, with every idea leading into the next with ease.