231 Best Grown-up Comedy Movies to Watch (Page 8)

Of the many violence-inflected black comedies that Pulp Fiction spawned, Grosse Pointe Blank ranks among the best. Though it’s patently inspired by Tarantino’s magnum opus — John Cusack plays a sardonic, amoral hitman, and the film features bursts of stylized violence and a retro soundtrack — it never feels derivative. The film finds its own identity as a quirky romcom when Cusack’s character, Martin Blank, returns to his hometown for a 10-year high-school reunion on the advice of his terrified therapist (Alan Arkin).

Martin is experiencing professional disillusionment as part of the quarter-life crisis that often takes hold when one realizes it’s been a whole decade since high school. His profession puts a darkly comic spin on that convention, but the film doesn’t treat that element entirely flippantly. Unlike Martin — and so many of the film’s Pulp Fiction-inspired brethren — Grosse Pointe Blank isn’t nihilistic, but quite sincerely romantic. Its hybrid nature and surprising heart come to the fore in Martin’s renewed relationship with the girlfriend he jilted at prom: Debi (Minnie Driver), now a ska-loving radio DJ. Cusack and Driver have sparkling chemistry, which makes the sincerity with which their characters grapple with the possibility of a second chance at happiness all the more absorbing to watch.

Genre: Action, Comedy, Drama, Romance, Thriller

Actor: Alan Arkin, Ann Cusack, Barbara Harris, Belita Moreno, Benny Urquidez, Bill Cusack, Bobby Bass, Carlos Jacott, Dan Aykroyd, David Barrett, Doug Dearth, Hank Azaria, Jenna Elfman, Jeremy Piven, Joan Cusack, John Cusack, K. Todd Freeman, Michael Cudlitz, Minnie Driver, Mitchell Ryan, Steve Pink

Director: George Armitage

Demonstrating that a great stand-up routine should always stem from strong writing first and foremost, Brian Simpson makes common subjects for ridicule feel fresh again—just through how clever his writing is. Simpson seems to position himself from the same place where more controversial comedians punch down at women and at queerness. But he manages to push against expectations by keeping his focus on those who normally don't get the brunt of the criticism, or by drawing us toward broader cultural problems that make people act the way that they do. None of this is all that novel, of course, and Simpson does end up dwelling on certain subjects for too long. But every line he speaks feels considered and is deployed with the perfect matter-of-factness, keeping the laughs consistent without ever complaining or intentionally trying to provoke.

Genre: Comedy

Actor: Brian Simpson

Director: Baron Vaughn

You don’t have to have seen a single game of tennis to enjoy this mockumentary about the longest match that (n)ever took place in the sport’s history. Andy Samberg plays Aaron Williams, the mullet-sporting adopted brother of Serena and Venus (whose family “reverse Blind-Sided” him) made immortal by his record-smashing, week-long battle with posh, dim-witted English prodigy Charles Poole (Kit Harington) at Wimbledon. Things only get more riotously ridiculous from the premise: the team behind sports spoof Tour de Pharmacy chronicle the winding journeys the rivals took to that climactic seven-day showdown, from forays into the world of innovative underwear design to stints in Swedish jails, by way of a surreal tangent into the storied faux-history of courtroom sketch art. Suffice it to say: the tennis isn’t really the point here.

Real-life figures from the sport (including Serena Williams and John McEnroe) ground the spoof in enough reality to make the zany humor pop, with the comedy coming from a very game Fred Armisen, Michael Sheen, Lena Dunham, Will Forte, and Howie Mandel. With eccentric humor in spades — from the puerile to the surreal — and a lean runtime, 7 Days in Hell packs in as many dizzying jokes as Aaron and Charles do volleys in their absurd history-making rally.

Genre: Comedy, TV Movie

Actor: Andy Samberg, Chris Evert, Chris Romano, David Copperfield, Destiny Soria, Dolph Lundgren, Filip Hammar, Fred Armisen, Howie Mandel, Jerry Gregorio, Jim Lampley, John McEnroe, Jon Hamm, June Squibb, Karen Gillan, Kit Harington, Lena Dunham, Ludwig Manukian, Lyssa Roberts, Mary Steenburgen, Michael Sheen, Serena Williams, Soledad O'Brien, Will Forte

Director: Jake Szymanski

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.

Genre: Comedy, Drama

Actor: Andrew Hawkins, Billy J. Mitchell, Billy Mitchell, Charlotte Zucker, Chas Bryer, Christopher Villiers, Dimitri Andreas, Eddie Powell, Eddie Tagoe, Gertan Klauber, Harry Ditson, Ian McNeice, Janos Kurucz, Jeremy Kemp, Jim Carter, John J. Carney, John Sharp, Lee Sheward, Lucy Gutteridge, Mac McDonald, Marcus Powell, Michael Gough, Nicola Wright, Omar Sharif, Orla Pederson, Peter Cushing, Richard Bonehill, Richard Mayes, Steve Ubels, Susan Breslau, Sydney Arnold, Tristram Jellinek, Val Kilmer, Warren Clarke

Director: David Zucker, Jerry Zucker, Jim Abrahams

Rating: PG

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.

Genre: Action, Comedy, Crime, Drama

Actor: Alessandra Mastronardi, Björn Freiberg, Caroline Boulton, Cesare Taurasi, David Gordon Green, Demi Moore, Eli Jane, Enrique Martínez, Ike Barinholtz, Jacob Scipio, Jaime Ordóñez, Joanna Bobin, Katrin Vankova, Kristian Flores, Kristian Ventura, Lily Mo Sheen, Manuel Tallafé, Mario Perez, Neil Patrick Harris, Nicholas Wittman, Nicolas Cage, Paco León, Pedro Pascal, Rebecca Finch, Ricard Balada, Sharon Horgan, Tiffany Haddish

Director: Tom Gormican

Rating: R

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.

Genre: Comedy, Drama, Romance

Actor: Adam Enright, Adrian Tomine, Ally Maki, Boran Anh, Debby Ryan, George Deihl Jr., Jacob Batalon, Jess Nahikian, Justin H. Min, Melanie J. Newby, Mike Cabellon, Nikhaar Kishnani, Randall Park, Ronny Chieng, Scott Seiss, Sheldon Best, Sherry Cola, Sonoya Mizuno, Stephanie Hsu, Tavi Gevinson, Theo Iyer, Timothy Simons

Director: Randall Park

Rating: R

This fun comedy-drama is about Bridget, a 34-year-old who hasn't quite got it all figured out, but at least she’s trying: after terminating an accidental pregnancy, she gets herself a summer gig as a nanny for a fearless six-year-old by the name of Frances. 

Tackling a myriad of "taboo" topics including abortion, menstruation, and depression, the movie visually normalizes human experiences that remain underrepresented in mainstream cinema. And writer Kelly O’Sullivan, who also plays Bridget, has a screenplay that manages to do it all without feeling didactic.

Genre: Comedy, Drama

Actor: Bradley Grant Smith, Charin Alvarez, Chris Coats, Courtney Rioux, Danny Catlow, Francis Guinan, H.B. Ward, Hanna Dworkin, Jackson Evans, Jim True-Frost, Kelly O'Sullivan, Lily Mojekwu, Mary Beth Fisher, Max Lipchitz, Meighan Gerachis, Noah Williams, Ramona Edith Williams, Rebecca Buller, Rebecca Spence, Rebekah Ward, Roger Welp, Sophia Rubin

Director: Alex Thompson

Rating: N/A