19 Best Comedy Movies to WatchMovies Like Punch-Drunk Love (2002) (Page 2)

Need a chuckle? We know comedy gold can be hard to come by, so we’ve scoured the depths of the streaming landscape to dig it out. From dark humor to laugh-out-loud misadventures, these are the best comedies to stream now.

Adam Sandler, though currently imminently marketable, incredibly played out and boring, used to be a real actor. This is the film by which his legacy will be judged, where we see the funnyman drop the mask and actually show real feelings besides bumbling rage. Sandler's hurt and confused performance is beautifully vulnerable and true and is complimented by P.T. Anderson's incomparable direction (the man behind Boogie Nights and There Will Be Blood), creating a true masterpiece of American cinema. This beauty also stars Philip Seymour Hoffman and Emily Watson.

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16. Ghost World, 2001

Based on the comic book by Daniel Clowes, Ghost World is a dark comedy that follows the exploits of teenage outcasts Enid and Rebecca (Thora Birch and Scarlett Johansson) as they navigate the many complexities of burgeoning adulthood. Central to the story is the unlikely friendship that Enid strikes up with a lonesome older man (played by Steve Buscemi), a curious relationship that drifts through various humorous and melancholy situations. It’s an original and often poignant look at alienation and identity, with Birch delivering a wonderfully deadpan and often hilarious performance, despite her entirely pessimistic attitude. It’s the type of film that’s just right when you’re in the mood for something just a little bit different.

Genre: Comedy, Drama

Actor: Alex Solowitz, Anna Berger, Ashley Peldon, Bob Balaban, Brad Renfro, Brett Gilbert, Brian George, Brian Jacobs, Bruce Glover, Chachi Pittman, Charles C. Stevenson Jr., Charles Schneider, Daniel Graves, Danny Allen, Dave Sheridan, David Cross, Debi Derryberry, Debra Azar, Diane Salinger, Dylan Jones, Ezra Buzzington, Illeana Douglas, Jake La Botz, James Sie, Jerry Rector, Joan Blair, Joel Michaely, John Bunnell, Joseph Sikora, Joshua Wheeler, Joy Bisco, Kaileigh Brielle Martin, Lauren Bowles, Lindsey Girardot, Lorna Scott, Marc Vann, Martin Grey, Mary Bogue, Matt Doherty, Pat Healy, Patrick Fischler, Paul Keith, Rini Bell, Scarlett Johansson, Sid Hillman, Stacey Travis, Steve Buscemi, T. J. Thyne, Teri Garr, Thora Birch, Tom McGowan, Tony Ketcham, Venus DeMilo Thomas, Will Forte

Director: Terry Zwigoff

Rating: R

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17. Happiness, 1998

Happiness is a difficult, disturbing watch. Unlike films that claim to be brave, Happiness actually goes there and shows us just how deep, dark, and perverse our urges can get. But far from being controversial for the sake of it, this fearless film has important things to say about the facade of happiness, the urgency of loneliness, and the futility of feigning ignorance about both. And it does so with an impressively wry humor delivered by a talented cast that includes Philip Seymour Hoffman, Lara Flynn Boyle, and Dylan Baker. They play their complicated characters so well, they'll have you thinking about the strange ways you can, in fact, relate to them on some level, long after the credits roll.

This isn't a film you'll want to revisit often, but you will have to see it at least once in a lifetime—if anything, for the kind of painful honesty you’ll rarely find anywhere else.

Genre: Comedy, Drama

Actor: Ann Harada, Anne Bobby, Arthur J. Nascarella, Ben Gazzara, Bina Sharif, Camryn Manheim, Cynthia Stevenson, Dan Moran, Diane Tyler, Douglas McGrath, Dylan Baker, Elizabeth Ashley, Gerry Becker, Jane Adams, Jared Harris, Joe Lisi, Johann Carlo, Jon Lovitz, José Rabelo, Justin Elvin, Lara Flynn Boyle, Lisa Louise Langford, Louise Lasser, Marina Gayzidorskaya, Marla Maples, Matt Malloy, Molly Shannon, Philip Seymour Hoffman, Rufus Read, Socorro Santiago, Todd Solondz, Wai Ching Ho

Director: Todd Solondz

Rating: NC-17

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18. Transamerica, 2005

Bree (Felicity Huffman) is an uptight transwoman who gets a phone call from her long lost son who is in trouble. She does not tell him she is his father but bails him out of jail and they end up on a long road trip to LA. Bree's high strung conservative personality intersecting with a wild young man and people they meet along the way leads to some comical situations. Felicity Huffman's performance is excellent. It is enjoyable to watch the characters develop over the film.

Genre: Comedy, Drama

Actor: Amy Povich, Andrea James, Bianca Leigh, Burt Young, Calpernia Addams, Carrie Preston, Craig Bockhorn, Danny Burstein, Elizabeth Peña, Elizabeth Peña, Felicity Huffman, Fionnula Flanagan, Forrie J. Smith, Graham Greene, Grant Monohon, Jim Frangione, Jon Budinoff, Kevin Zegers, Maurice Orozco, Paul Borghese, Raynor Scheine, Richard Poe, Stella Maeve, Steve Hurwitz, Teala Dunn, Venida Evans

Director: Duncan Tucker

Rating: R

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19. The Royal Tenenbaums, 2001

In this ensemble cast directed by Wes Anderson, we see a very dysfunctional family with three very unique siblings who grow apart from each other due to their father, a charismatic and ever-absent grifter. However, when he announces his immanent death, the whole family is forced to confront each other, themselves and their childhoods as they gather in their patriarchal home together for the first time in years. An absolutely gorgeously filmed movie, the usage of color, pattern and 60's rock music alone makes it worth seeing, and the beautiful story just sweetens the deal.

Genre: Comedy, Drama

Actor: Al Thompson, Alec Baldwin, Amir Raissi, Andrew Wilson, Anjelica Huston, Ben Stiller, Bill Murray, Brian Smiar, Brian Tenenbaum, Danny Glover, Dipak Pallana, Don McKinnon, Donal Lardner Ward, Ebon Moss-Bachrach, Eric Chase Anderson, Frank Wood, Gary Evans, Gene Hackman, Grant Rosenmeyer, Greg Goossen, Guido Venitucci, Gwyneth Paltrow, Irina Gorovaia, Jennifer Wachtell, Jonah Meyerson, Kalani Queypo, Keith Charles, Kumar Pallana, Larry Pine, Liam Craig, Luke Wilson, Max Faugno, Mel Cannon, Nova Landaeus-Skinnar, Owen Wilson, Pawel Wdowczak, Rex Robbins, Roger Shamas, Rony Clanton, Saidah Arrika Ekulona, Sam Hoffman, Seymour Cassel, Sheelagh Tellerday, Sonam Wangmo, Stephen Dignan, Stephen Lea Sheppard, Tatiana Abbey, Tom Lacy, Wes Anderson, 吉恩·哈克曼

Director: Wes Anderson

Rating: R

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