20 Movies Like O Brother Where Art Thou? (2000)

Staff & contributors

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.

Genre: Comedy, Drama, Romance, Thriller

Actor: Adam Sandler, David H. Stevens, Don McManus, Emily Watson, Hazel Mailloux, Jason Andrews, Jonathan Loughran, Karen Kilgariff, Larry Ring, Luis Guzman, Mary Lynn Rajskub, Nathan Stevens, Philip Seymour Hoffman, Rico Bueno, Robert Smigel

Director: Paul Thomas Anderson

Rating: R

You might expect a movie about the Irish struggle for independence from the British Empire during the 1920s to be a sweeping historical epic a la Braveheart, but The Wind That Shakes The Barley is instead a heartbreaking miniature portrait of the human impact that the brutal occupation has on the residents of a small County Cork village. Cillian Murphy is superb as Damien O’Donovan, a young medical student who is about to up sticks for London when he witnesses first-hand the savagery of British forces on his neighbors. Galvanized into action, he joins the local branch of the IRA, which is led by his brother Teddy (Pádraic Delaney).

What makes The Wind That Shakes The Barley so potent isn’t just its depiction of the fierce local rebellion that Damien and his comrades wage against the British forces — it’s also its gutting exploration of the cyclical war that began to rage amongst the freedom fighters once the British left. As Damien puts it, “It's easy to know what you're against, quite another to know what you're for” — a dilemma that wedges the two brothers apart to bitter ends.

Genre: Drama, War

Actor: Aidan O'Hare, Antony Byrne, Cillian Murphy, Denis Conway, Frank O'Sullivan, Keith Dunphy, Liam Cunningham, Noel O'Donovan, Orla Fitzgerald, Pádraic Delaney, Roger Allam, Sean McGinley, Shane Casey, Siobhan McSweeney, Tom Charnock

Director: Ken Loach

David O. Russel (Silver Linings Playbook, American Hustle) is one of those directors who the more you dig into his past, the more you are rewarded. I Heart Huckabees is a great example of this, as is The Fighter (both are must-watch if you haven't seen them). But it is Three Kings that truly presented him as someone who can give great substance to big-budget movies. It stars George Clooney, Mark Wahlberg, Ice Cube, and even director Spike Jonze (Her, Adaptation), in other words, a festival of talent at its peak. And it follows three soldiers who want use the end of the Gulf War as an opportunity to get rich. Their journey through a devastated and uncertain Iraq is a thrilling one, as Three Kings is action-packed. But the purpose of this movie lies somewhere between political satire around American interventionism and social criticism of the main characters. However, none of that stands in the way of this movie being an entertaining and exhilarating movie.

Genre: Action, Comedy, War

Actor: Ali Afshar, Alia Shawkat, Brian Bosworth, Cliff Curtis, David O. Russell, Doug Jones, Dylan Brown, George Clooney, Holt McCallany, Ice Cube, Jamie Kennedy, Jim Gaffigan, Jon Sklaroff, Judy Greer, Liz Stauber, Mark Wahlberg, Mykelti Williamson, Nora Dunn, Rick Shuster, SaÁ¯d Taghmaoui, Saïd Taghmaoui, Sayed Badreya, Spike Jonze

Director: David O. Russell

Rating: R

As black a comedy as they come. Nick Naylor (superbly portrayed by Aaron Eckhart) is the chief spokesperson for tobacco and shows the world why smoking is as key to protect as any other liberal value. This movie is funny, smart, thoughtful and raises some good questions about the ego, the morale and what we leave behind, from unexpected sides.

Genre: Comedy, Drama

Actor: Aaron Eckhart, Aaron Lustig, Adam Brody, Aloma Wright, Brian Palermo, Bruce French, Cameron Bright, Catherine Reitman, Connie Ray, Courtney Taylor Burness, Dana E. Glauberman, Daniel Travis, David Koechner, David O. Sacks, Dennis Miller, Earl Billings, Elon Musk, Eric Haberman, Eva La Dare, J.K. Simmons, Jeff Witzke, Joan Lunden, Jordan Garrett, Katie Holmes, Kim Dickens, Marc Scizak, Maria Bello, Marianne Muellerleile, Mary Jo Smith, Melora Hardin, Michael Mantell, Nancy O'Dell, Rachel Thorp, Renée Graham, Richard Speight Jr., Rob Lowe, Robert Duvall, Roy Jenkins, Sam Elliott, Sean Patrick Murphy, Spencer Garrett, Terry James, Timothy Dowling, Todd Louiso, William H. Macy

Director: Jason Reitman

Rating: R

A delightfully screwy comedy about a guy and his struggling bar (of the title). The film is full of food, music, dancing, romance, and crazy coincidences. Our hero, Zinos, has just be abandoned by his girlfriend. On top of that his bar is struggling, he’s recently thrown his back out, he desperately needs to find a new chef, and his shady brother has just come to the Soul Kitchen looking for a job after being let out of on “partial parole.” Will it all work out in the end? Of course it will! This film is a lot lighter than Akin’s previous features, but maybe after all those challenging pictures he just felt the need to have a good time, which this film definitely delivers.

Genre: Comedy, Drama

Actor: Adam Bousdoukos, Anna Bederke, Birol Ünel, Birol Ünel, Catrin Striebeck, Cem Akin, Demir Gökgöl, Demir Gökgöl, Dorka Gryllus, Gustav-Peter Wöhler, Hendrik von Bültzingslöwen, Herma Koehn, Jan Fedder, Lars Rudolph, Lucas Gregorowicz, Marc Hosemann, Maria Ketikidou, Markus Imboden, Monica Bleibtreu, Moritz Bleibtreu, Peter Jordan, Peter Lohmeyer, Pheline Roggan, Philipp Baltus, Simon Görts, Till Huster, Udo Kier, Uğur Yücel, Wotan Wilke Möhring, Wotan Wilke Möhring, Zarah Jane McKenzie

Director: Fatih Akin

Rating: N/A, Unrated

If it weren’t for his knack for writing, Max Fischer (Jason Schwartzman) would never have gotten into a prep school like Rushmore. But his art secures him a scholarship, and what he lacks in smarts and money, he makes up for in school pride. As he flunks more and more of his academics, however, he is eventually kicked out, and it’s outside the halls of his beloved Rushmore, stripped of all titles and insignia, where he learns to be his true self.  

As the film’s comedic and emotional core, Schwartzman is a revelation as the ambitious and sharp-tongued Max. Equally captivating is Bill Murray’s deadpan but lovable turn as Max’s millionaire friend, Herman Blume. It’s a role so fitting, in fact, that the poor-rich-man character will follow Murray well into his career, long after the curtains close on Mr. Blume. Meanwhile, Wes Anderson will go on to do more colorful and stylized pictures than Rushmore, but thanks to its unbeatable wit and down-to-earth charm, the film remains to be one of the auteur’s most delightful and hilarious works to date. 

Genre: Comedy, Drama

Actor: Alexis Bledel, Andrew Wilson, Antoni Scarano, Bill Murray, Brandon Trost, Brian Cox, Brian Tenenbaum, Connie Nielsen, Dipak Pallana, Ed Geldart, Eric Chase Anderson, George Farish, Jason Schwartzman, Jason Trost, Kim Terry, Kumar Pallana, Lucille Sadikin, Luke Wilson, Marietta Marich, Mason Gamble, Olivia Williams, Paul Schiff, Sara Tanaka, Seymour Cassel, Stephen Dignan, Stephen McCole, Wallace Wolodarsky

Director: Wes Anderson

This forgotten gem is the perfect family movie. It stars Michael Caine and Robert Duvall as the two eccentric uncles of Walter, a shy city kid (played by Haley Joel Osment). When Walter moves in with his uncles in rural Texas, he first has a hard time adjusting to his new surroundings. However his routine is changed after he starts hearing local gossip about his uncles, and reminiscence spurs in all three an incredible eagerness for adventure. Secondhand Lions has gathered impressive cult following in the past few years, and rightfully so. Its fast-paced, entertaining yet substantial storyline shines a light on the amazing performances by the cast, and offers a surprising mix of funny, heartwarming and sad. Look out for the flashback scenes.

Genre: Comedy, Drama, Family

Actor: Adam Ozturk, Adrian Pasdar, Billy Joe Shaver, Brian Stanton, Christian Kane, Dameon Clarke, Deirdre O'Connell, Deirdre OConnell, Emmanuelle Vaugier, Eric Balfour, Eugene Osment, Haley Joel Osment, Jason Douglas, Jennifer Stone, Jo Harvey Allen, Joe Stevens, Josh Lucas, Kanin Howell, Kevin Haberer, Kyra Sedgwick, Marc Musso, Michael Caine, Michael O'Neill, Mitchel Musso, Morgana Shaw, Nick Price, Nicky Katt, Rick Dial, Robert Duvall, Rory Thost, Travis Willingham

Director: Tim McCanlies

Rating: PG

Best in Show’s cast list reads like a catalog of comic greats. Among others, it includes Parker Posey, Jane Lynch, John Michael Higgins, Jennifer Coolidge, and the unbeatable duo that is Catherine O’Hara and Eugene Levy. Their participation alone should you clue in on what kind of film this is: a delightful exercise in improvisational comedy. The jokes roll in fast and the spoofs are spot-on (Parker Posey gets a special mention for playing the faux-calm handler with rage issues bubbling up to a tee). And thanks to the mockumentary format, they’re supported by an abundance of visual gags. 

The cherry on top of this fun sundae is the adorable dogs who amusingly participate in human shenanigans. If you're ever looking for a watch that is equal parts comedic and cute, then this underrated comedy gem of a film could be it.

Genre: Comedy, Drama

Actor: Andrew Johnston, Andrew Wheeler, Bob Balaban, Camille Sullivan, Carmen Aguirre, Carrie Aizley, Catherine O'Hara, Christopher Guest, Colin Cunningham, Corrine Koslo, Deborah Theaker, Doane Gregory, Don Lake, Don S. Davis, Ed Begley Jr., Eugene Levy, Fred Willard, Fulvio Cecere, Hiro Kanagawa, Jane Lynch, Jay Brazeau, Jennifer Coolidge, Jim Piddock, John Michael Higgins, Larry Miller, Lewis Arquette, Linda Kash, Lynda Boyd, Malcolm Stewart, Merrilyn Gann, Michael Hitchcock, Michael McKean, Parker Posey, Patrick Cranshaw, Rachael Harris, Scott Williamson, Stephen E. Miller, Steven M. Porter, Teryl Rothery, Tony Alcantar, Will Sasso

Director: Christopher Guest

Rating: PG-13

The Promise has all the trappings of a sleazy crime drama, but there's a sense of innocence buried underneath all the dirt that helps set it apart. Even as Igor helps his father do the shadiest things to exploit the illegal immigrants under their care, you can see the boy slowly wake up to the realization that life can't just be a series of transactions, rewards, and punishments. As writers and directors, the Dardenne brothers present Igor's coming of age with frankness and without pretension—even when a hint of the mystical begins to compel him to tell the truth. It might not seem all that complex at first, but the details that make up this world are fully immersive from start to finish.

Genre: Drama

Actor: Frédéric Bodson, Jean-Michel Balthazar, Jérémie Renier, Norbert Rutili, Olivier Gourmet, Sophia Leboutte

Director: Jean-Pierre Dardenne, Luc Dardenne

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, Bonnie Rose, Bradley Mott, Carey Mulligan, Declan Bennett, Ethan Phillips, F. Murray Abraham, Garrett Hedlund, Helen Hong, Jack O'Connell, Jake Ryan, Jeanine Serralles, Jerry Grayson, John Goodman, Justin Timberlake, Max Casella, Oscar Isaac, Ricardo Cordero, Robin Bartlett, Stark Sands, Sylvia Kauders

Director: Ethan Coen, Joel Coen

Rating: R

This is an inexplicably and philosophically dark comedy.

Its protagonist, Larry, is a lackluster professor at a dull university. Then his life starts to unravel: his wife decides to leave him for one of his more successful colleagues; his unemployed brother moves in to stay on his couch.

So Larry ventures on a quest for meaning and clarity within his Jewish community.

All Cohen Brothers fans will appreciate the movie's aesthetics and comedic strength. The protagonist’s struggle will resonate with anyone who has had a religious upbringing: guilt is a big theme here.

I felt like I had to rewatch it to understand it. But I also enjoyed that weird sense of not understanding everything that's going on. Much like life itself.

The film rightfully earned itself two nominations for the Oscars, including Best Picture.

Genre: Comedy, Drama

Actor: Aaron Wolff, Adam Arkin, Alan Mandell, Allen Lewis Rickman, Amanda Day, Amy Landecker, Brent Braunschweig, Claudia Wilkens, Fred Melamed, Fyvush Finkel, George Wyner, Jessica McManus, Joel Thingvall, Katherine Borowitz, Landyn Banx, Michael Lerner, Michael Stuhlbarg, Peter Breitmayer, Punnavith Koy, Raye Birk, Richard Kind, Sari Lennick, Simon Helberg, Stephen Park, Steve Park, Yelena Shmulenson

Director: Ethan Coen, Joel Coen

Rating: R

One of those long-lost mid-budget dramas that's content with observing the rich yet uneventful lives of average folk, Nobody's Fool reminds us that nothing exciting or shocking needs to happen to make a good story. The late, eternally charismatic Paul Newman leads an ensemble of character actors in relaxed, memorable roles—Bruce Willis, Philip Seymour Hoffman, Margo Martindale, and Jessica Tandy, among others. It's the authentic, neither-love-nor-hate relationship among all these characters that drives all their individual drama forward and keeps the film from stagnating into anything less than endearing. Here, the idea of things never really changing in this small community is meant to be a comfort, not a lament.

Genre: Comedy, Drama

Actor: Alexander Goodwin, Alice Drummond, Angela Pietropinto, Angelica Page, Anibal O. Lleras, Bruce Willis, Carl J. Matusovich, Catherine Dent, Dylan Walsh, Elizabeth Wilson, Gene Saks, Gerry Robert Byrne, Jay Patterson, Jerry Mayer, Jessica Tandy, Josef Sommer, Marcus Powell, Margo Martindale, Melanie Griffith, Page Johnson, Paul Newman, Philip Bosco, Philip Seymour Hoffman, Pruitt Taylor Vince, Richard Mawe, Shannah Laumeister Stern

Director: Robert Benton

, 2017

This fun drama is about a 90-year-old who’s still searching for answers to life’s existential questions. Lucky smokes, drinks, and is pretty angry (a not-so-chill atheist); but he’s still around.

Harry Dean Stanton, in what feels like an extension to his character Lucky, passed away a year after the film premiered in 2017. This was the last role of the legendary Alien and The Godfather actor.

Genre: Drama

Actor: Ana Mercedes, Barry Shabaka Henley, Bertila Damas, Beth Grant, David Lynch, Ed Begley Jr., Harry Dean Stanton, Hugo Armstrong, James Darren, Ron Livingston, Tom Skerritt, Yvonne Huff

Director: John Carroll Lynch

Rating: Not Rated

Set in the 1930's English Countryside, the story of the eccentric Mortmain family is told from the daughter Cassandra's point of view. Her father, a once acclaimed and famous writer has written nothing in years, leading the family into bankruptcy. Themes such as first love and financial troubles are explored from Cassandra's comic and intelligent point of view. A classic and a must-see.

Genre: Drama, Romance

Actor: Alice Marie Crowe, Anna Paquin, Bijou Phillips, Bill Nighy, Billy Crudup, Christopher Ettridge, David Bamber, Dolly Wells, Eion Bailey, Eric Stonestreet, Fairuza Balk, Frances McDormand, Helena Little, Henry Cavill, Henry Thomas, James Faulkner, Jason Lee, Jay Baruchel, Jean Warren, Jimmy Fallon, Joe Sowerbutts, John Patrick Amedori, Kate Hudson, Kevin Sussman, Marc Blucas, Marc Maron, Michael Angarano, Noah Taylor, Patrick Fugit, Pauley Perrette, Philip Seymour Hoffman, Rainn Wilson, Ray Porter, Romola Garai, Rose Byrne, Sarah Woodward, Sinead Cusack, Sophie Stuckey, Tara Fitzgerald, Terry Chen, Zack Ward, Zooey Deschanel

Director: Cameron Crowe, Tim Fywell

Rating: R

A crazy, high-speed movie about double-dealing crooks and thieves living along the Danube River in Serbia. Such a description probably makes this movie sound dark and menacing, trust me it is anything but. It is filled to the brim with delightful music, slapstick humor, bizarre contraptions, shotgun weddings -- with a sweet romantic caper at its center. If winter weather is getting you down, consider watching this film as a fun & sunny antidote.

Genre: Comedy, Crime, Romance

Actor: Bajram Severdžan, Bajram Severdzan, Branka Katić, Branka Katic, Florijan Ajdini, Jasar Destani, Jashar Destani, Ljubica Adžović, Ljubica Adzovic, Miki Manojlović, Predrag Laković, Sabri Sulejmani, Salija Ibraimova, Srdjan 'Zika' Todorovic, Srdjan Todorovic, Srđan Todorović, Zabit Memedov

Director: Emir Kusturica

Rating: R