31 Best Quarter life crisis movies Movies to Watch (Page 2)

«When comedians get a bit older they do a movie with “emotions” in it. Here’s mine.» Flight of the Conchords’ Jemaine Clement on Twitter. People Places Things is exactly that, a funny yet heartfelt comedy. Will Henry, A New York City graphic novelist walks in on his girlfriend cheating on him at their kids’ birthday party. A year later, Will is struggling to define his new life as a single parent while still getting over his breakup. Smart, honest, and led by Jemaine Clement, this film will strike you in its simplicity but will hold you with its charm.

Genre: Comedy, Drama, Romance

Actor: Aundrea Gadsby, Celia Au, Derrick Arthur, Dionne Audain, Gavin Haag, Gia Gadsby, Jemaine Clement, Jessica Williams, Matthew Maher, Michael Chernus, Nancy Eng, Paul Castro Jr., Regina Hall, Samantha Posey, Stephanie Allynne

Director: Jim Strouse

Rating: R

If you’ve seen his stand-up, you’ll know that Pete Davidson likes to make fun of himself. But it’s also true that Davidson is honest. He speaks openly about his childhood traumas and mental health struggles, and this film about his life is no different than his live performances. It's darkly funny and deeply personal, this time plumbing new depths of his life with the help of director (and patron saint of comedians) Judd Apatow. 

Here, Apatow allows Davidson to hell his story in his own irreverent flavor, all while boosting him with directorial flair and his trademark balance of humor and humanity. A triumphant collaboration between Apatow and Davidson, King of Staten Island is rich with nuanced performances and relatable insights into the life of someone slowly but surely healing from pain and coming into his own. 

Genre: Comedy, Drama

Actor: Action Bronson, Adam Keane, Alexis Rae Forlenza, Angus Costello, Anthony Lee Medina, Bel Powley, Bill Burr, Bonnie McFarlane, Carly Aquilino, David S. Lomax, Derek Gaines, Domenick Lombardozzi, Gina Jun, Hank Strong, Jack Hamblin, Jessica Kirson, Jimmy Tatro, Keith Robinson, Ken Holmes, Kevin Corrigan, Laurence Blum, Lilly Brown, Liza Treyger, Lou Wilson, Luke David Blumm, Lynne Koplitz, Machine Gun Kelly, Marilyn Torres, Mario Polit, Marisa Tomei, Maude Apatow, Melania Zalipsky, Meredith Handerhan, Michelle Sohn, Mike Vecchione, Moises Arias, Nana Mensah, Nils Johnson, Nina Hellman, Nyla Durdin, Pamela Adlon, Pauline Chalamet, Pete Davidson, Rafael Poueriet, Rich Vos, Ricky Velez, Robert Smigel, Steve Buscemi, Teodorina Bello

Director: Judd Apatow

Rating: R

Slow and almost silent, Edward Yang’s second feature film pins us down in a fast-moving city. In 1980s Taipei, Chin and Lung are childhood sweethearts who try to build a life together, but differences between their wants threaten to pull them apart. Chin bravely adapts to the changes she faces—moving house, shifting jobs, etc.—while Lung misses his promising baseball career and prioritizes familial debt. Through their relationship, the film captures the anxieties of a generation pulled between new Western consumerism and old Asian familial obligations. Watching the two lovers feels like being lost in a cold urban city, unable to move and not knowing where to go.

Genre: Drama

Actor: Chen Shu-fang, Chin Tsai, Cynthia Khan, Grace Chen Shu-Fang, Hou Hsiao-hsien, Ko I-chen, Ko Su-yun, Lin Hsiu-ling, Mei Fang, Peng Sun, Su-Yun Ko, Tsai Chin, Wu Nien-Jen, Yang Li-yin, 吴念真

Director: Edward Yang

Rating: Not Rated

Like a Wes Anderson movie, The Last Black Man in San Francisco takes artistic risks and nails every one of them. There are many quirky, aesthetically well-studied, and even funny aspects to this moving story.

Jimmie has been maintaining a typical San Francisco Victorian house, regularly painting the windows and watering the plants. One small problem: other people live there and they don’t want him around. It turns out this was once Jimmie’s family house, having been built by his grandfather in 1948, and he misses it deeply.

This story is based on writer Jimmie Fails’ life, as he tried to reclaim his family home in SF. However, it’s not a movie that limits itself to gentrification. It transcends that to being about the universal yearning to find a place to call home.

Genre: Drama

Actor: Andy Roy, Daewon Song, Danny Glover, Finn Wittrock, Isiain Lalime, Jamal Trulove, Jello Biafra, Jimmie Fails, John Ozuna, Jonathan Majors, Mari Kearney, Mike Epps, Rob Morgan, Thora Birch, Tichina Arnold, Tonya Glanz, Warren Keith

Director: Joe Talbot

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, Daniel Hank, 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

Inside Llewyn Davis tells the interesting and captivating story of a young, struggling singer navigating through the Greenwich Village folk scene in 1961. The movie conveys all sorts of emotions, thanks to Coen brothers’ stroke of genius: it is strange, funny, dramatic and satisfying at the same time. Not to mention, the ensemble cast is superb, and the music is absolutely great. It is the kind of movie that will put an unfamiliar yet wondrous feeling into you as you live through Llewyn Davis' eyes and feel his pain.

Genre: Drama, Music

Actor: Adam Driver, Alex Karpovsky, Benjamin Pike, Bonnie Rose, Bradley Mott, Carey Mulligan, Charlotte Booker, Declan Bennett, Diane Findlay, Ethan Phillips, F. Murray Abraham, Frank Ridley, Garrett Hedlund, Helen Hong, Ian Blackman, Ian Jarvis, Jack O'Connell, Jake Ryan, James Colby, Jeanine Serralles, Jerry Grayson, John Ahlin, John Goodman, Justin Timberlake, Marcus Mumford, Max Casella, Mike Houston, Oscar Isaac, Ricardo Cordero, Roberto Lopez, Robin Bartlett, Sam Haft, Stark Sands, Stephen Payne, Steve Routman, Susan Blommaert, Sylvia Kauders

Director: Ethan Coen, Joel Coen

Rating: R

In Compartment Number 6, two different people strike an unlikely friendship during a train ride from Moscow to Murmansk. One is Laura, a Finnish student looking to observe ancient rock carvings at their destination, and the other is Ljoha, a gruff miner who hopes to secure a job once there. While the pair are initially unable to get on the same page, their friction eventually lends way to curiosity and empathy, especially as they learn more about each other and life itself.

It’s a great film to put on if you’re a fan of smart but subdued movies like the Before trilogy and Lost in Translation, and there is a lot to mine beyond their already-rich conversations, especially in terms of class and romance. It’s little wonder then that this delightful two-hander shares the 2021 Grand Prix award with another brilliant piece of art, Asghar Farhadi's A Hero.

Genre: Drama

Actor: Denis Pyanov, Dinara Drukarova, Galina Petrova, Konstantin Murzenko, Mikhail Brashinsky, Natalia Drozd, Polina Aug, Seidi Haarla, Sergey Agafonov, Tomi Alatalo, Valeriy Nikolaev, Yuliya Aug, Yuriy Borisov

Director: Juho Kuosmanen

Rating: R

Miso may be living day to day on her meager earnings as a cleaner, but she is decidedly content. She insists that all she needs to get by are cigarettes, whiskey, and time with her boyfriend, so when a spike in rent and prices invites her to reassess her priorities, she doesn’t budge. Instead of forgoing these luxuries, she gives up her tiny place and couch surfs with her old bandmates. What follows is a reunion of sorts, where darkly humorous epiphanies are had on both ends about adulthood, responsibilities, and what it really means to be happy in an increasingly indifferent, profit-oriented world.  

Microhabitat treads on very grave themes, and the images it conjures can be unsettling. But it is also surprisingly light on its feet, displaying sharp satire and sweet empathy for its unyielding protagonist. Miso is portrayed with a smartness and softness that evades rational judgment, and this endearment makes the story, especially the ending, all the more painfulul, poignant, and impactful.

Genre: Drama, Romance

Actor: Ahn Jae-hong, An Jae-hong, Cho Soo-hyang, Choi Deok-moon, Esom, Hwang Mi-young, Jang Sung-kyu, Kang Jin-ah, Kim Hee-won, Kim Jae-hwa, Kim Jae-rok, Kim Kuk-hee, Kim Yae-eun, Lee Seong-wook, Lee Sung-wook, Lee Yo-sup, Lee Yong-nyeo, Park Ji-young, Woo Moon-gi

Director: Jeon Go-woon

Rating: Not Rated

Before “burnout,” “bullshit jobs,” and “quiet quitting” became part of our everyday lexicon, there was a film in the ‘90s that prophesied the rise of these workplace problems. Office Space follows three co-workers who, having had enough of their dreary low-paying jobs, fight back against their company via an embezzlement scheme. 

Office Space makes the most out of its indie budget as it mostly takes place in the cramped quarters of a company, effectively bottling us into the cubicled windowless world of the characters. But the real beauty of the film is in the details, from its quick zingers and thoughtful takes on the essence of work down to its elaborate “planning to plan” scheme in the background and the employees’ forced politeness singing happy birthday to their boss. Modern viewers will notice that Office Space sits right in between the dystopian thriller Severance and the beloved sitcom The Office—a dark comedy that highlights the necessity of humanity in everyday work. 

Genre: Comedy, Drama

Actor: Ajay Naidu, Alexandra Wentworth, Ali Wentworth, Barbara George-Reiss, Cassie Townsend, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Heath Young, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Josh Bond, Justin Possenti, K. Todd Lytle, Kinna McInroe, Kyle Scott Jackson, Linda Wakeman, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, R.C. Keene, Richard Riehle, Ron Livingston, Rupert Reyes, Samantha Inoue Harte, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R

Primarily, Cha Cha Real Smooth follows Andrew (Cooper Raiff) as he figures out what to do with his life post-college. But peripherally, it’s also about love, friendship, coming of age, and parenthood. Sometimes the movie wobbles under the weight of all it wants to be and you start to wonder whether it would benefit from a leaner script and a tighter focus. 

But ultimately, Cha Cha Real Smooth is endearing and a breeze to watch. Andrew is relatable as a know-it-all who doesn’t actually know it all, and Domino (Dakota Johnson) is moving as a young mother consumed by both her envy and love for Andrew. Despite its occasional unevenness, the film’s big emotional heart triumphs, and sometimes that’s the best that you can hope for in a story about one’s 20s.

Genre: Comedy, Drama, Romance

Actor: Amara Pedroso, Brad Garrett, Chris Newman, Colton Osorio, Cooper Raiff, Corrie Danieley, Dakota Johnson, Davina Reid, Evan Assante, John Paul Hurley, Jonathan Berry, Kelly O'Sullivan, Leslie Mann, Lisa Velten Smith, Odeya Rush, Raúl Castillo, Tommy Lafitte, Vanessa Burghardt

Director: Cooper Raiff

Rating: R

This is a revelation of a movie for its simplicity in handling a pretty serious and dark subject. It's the story of a generally immature and newly unemployed stand-up comic in New York and her unplanned pregnancy with a man that was supposed to be a fling, and it's surprisingly funny and yet rather touching. I can't think of many actresses who would've fit the bill quite like Jenny Slate. Not only is she hilarious, but her treatment of a generally sensitive issue from the honest, crass point of view of a down-on-life, New York-er leaves you drowning in empathy for her. I recommend this for anyone looking to cuddle up, have a few little clever laughs and feel all tingly in the chest-al area.

Genre: Comedy, Romance

Actor: Amy Novondo, Cindy Cheung, David Cross, Elise Widerker, Emily Tremaine, Ernest Mingione, Gabe Liedman, Gaby Hoffmann, Jake Lacy, Jennifer Kim, Jenny Slate, Justin Lerner, Karen Maine, Kitty Crystal, Mary DelMarco, Michael Bonfiglio, Nicholas Cirillo, Paul Briganti, Polly Draper, Richard Kind, Sarina Roma, Stacey Sargeant, Stephen Singer, Suzanne Lenz

Director: Gillian Robespierre

Rating: R

As Nicole Holofcener's directorial debut, Walking and Talking stands out not only for its honest dialogue and wonderful performance from the young Catherine Keener, but also for its portrayal of female friendship in a genre which too often portrays mindless cliches. The movie focuses on two best friends as one of them gets engaged and the other fears their friendship is getting lost in the middle of the excitement around her friend's marriage. Catherine Keener does a brilliant job as the likable but depressed friend and Anne Heche does an equally as good job playing her sympathetic half. A great movie if you're in the mood for something sweet, honest and sometimes sad.

Genre: Comedy, Drama, Romance

Actor: Alice Drummond, Allison Janney, Amy Braverman, Anne Heche, Bettina Skye, Brenda Denmark, Catherine Keener, Harold Ramis, Heather Gottlieb, Joseph Siravo, Kevin Corrigan, Liev Schreiber, Lynn Cohen, Miranda Rhyne, Rafa Alvarez, Randall Batinkoff, Todd Field, Vincent Pastore

Director: Nicole Holofcener

Rating: R

It’s very interesting, if not startling, to see an earnest movie made about the white upper class these days. Metropolitan is one such film, and even though it was released in the ’90s, it still stands the test of time precisely because it neither judges nor defends the group of WASPs it follows. It simply shows them in all their elegance and sophistication, as well as their insulation and irony. 

Metropolitan takes place in the upper crust of New York debutante society, during Christmas vacation, where soirees are rampant and afterparties even more so. The young-adult leads who navigate the scene in their expensive clothes and self-important aura recall a Scott Fitzgerald novel, or if you like, Gossip Girl episode. But instead of falling into tragedies, these characters just end up in silly but relatable mishaps and misunderstandings: they’re just kids after all. And as high and mighty as they may seem, whiling away in tall Park Avenue apartments, they’re still prone to the universal pains that haunt and shape teenagers. Expect to see heartbreak, jealousy, and longing even among the brightest and wealthiest of New York. 

Genre: Comedy, Drama, Romance

Actor: Alice Connorton, Bryan Leder, Carolyn Farina, Chris Eigeman, Donal Lardner Ward, Edward Clements, Francis Creighton, Isabel Gillies, Taylor Nichols, Thomas R. Voth, Will Kempe

Director: Whit Stillman

Rating: PG-13

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!

Genre: Comedy, Drama, Romance

Actor: Adam Rose, Adhir Kalyan, Adrienne Lamping, Amy Morton, Anna Kendrick, Chris Lowell, ​Christopher Lowell, Cut Chemist, Danny McBride, Dave Engfer, George Clooney, J.K. Simmons, Jason Bateman, Jeff Witzke, Jerry Vogel, Marvin Young, Matt O'Toole, Melanie Lynskey, Sam Elliott, Steve Eastin, Tamala Jones, Thomas M. Martilotti, Vera Farmiga, Zach Galifianakis

Director: Jason Reitman

Rating: R