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

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, Joji Yoshida, Jonathan Loughran, Karen Kilgariff, Larry Ring, Luis Guzman, Mary Lynn Rajskub, Nathan Stevens, Philip Seymour Hoffman, Rico Bueno, Robert Smigel, Shelley Waggener

Director: Paul Thomas Anderson

Rating: R

Don’t be fooled by its obvious parallels to Ghost (not a bad film, but a very different one): Truly, Madly, Deeply isn’t much concerned with the supernatural logistics of its back-from-the-dead-boyfriend premise, and it doesn’t feature any psychics or murders, either. In fact, there’s an argument to be made that everything that takes place here happens in its protagonist's imagination — that’s how much it ignores the ‘how’ of it all.

Instead, this deeply warm rom-com from the great Anthony Minghella grapples head-on with the emotional challenges of grief and moving on. Juliet Stevenson’s performance as the bereft Nina is up there as one of the most moving portrayals of loss the screen has seen, and not just because of how believable her intense cry-acting is. When she realizes her deceased boyfriend Jamie (Alan Rickman, as seductive and sardonic as always) has returned to the land of the living, her euphoria brings to aching life the dream that everyone who’s ever lost a loved one must surely have dreamt: how joyous it would be to see them again. Blending such raw observations with wry humor — and anchored by two leads with genuine chemistry — this is a profoundly moving and rewarding movie.

Genre: Comedy, Drama, Fantasy, Romance, TV Movie

Actor: Alan Rickman, Arturo Venegas, Bill Paterson, Christopher Rozycki, David Ryall, Deborah Findlay, Eddie Vincent, Frank Baker, Heather Williams, Jenny Howe, Juliet Stevenson, Keith Bartlett, Mark Long, Michael Maloney, Nitin Ganatra, Richard Syms, Stella Maris, Teddy Kempner, Terry Molloy, Tony Bluto, Vania Vilers

Director: Anthony Minghella

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, Alex Dee, Anthony Mark Streeter, Antony Byrne, Bill Hurst, Cillian Murphy, Colin Parry, Damien Kearney, Denis Conway, Frank Bourke, Frank O'Sullivan, Gerard Kearney, Keith Dunphy, Liam Cunningham, Mark Wakeling, Martin Lucey, Mary Murphy, Myles Horgan, Neil Alan Taylor, Noel O'Donovan, Orla Fitzgerald, Pádraic Delaney, Roger Allam, Sabrina Barry, Scott Peden, Sean McGinley, Shane Casey, Siobhan McSweeney, Tom Charnock, William Ruane

Director: Ken Loach

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, Robert Malina, Roy Jenkins, Sam Elliott, Sean Patrick Murphy, Spencer Garrett, Terry James, Timothy Dowling, Todd Louiso, William H. Macy

Director: Jason Reitman

Rating: R

Genre: Comedy, Drama

Actor: Adam Bousdoukos, Anna Bederke, Bernd Gajkowski, 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

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

Genre: Drama, Music

Actor: Adam Driver, Alex Karpovsky, Benjamin Pike, Bonnie Rose, Bradley Mott, Carey Mulligan, Charlotte Booker, Declan Bennett, 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

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, Drenda Spohnholtz, Dylan Walsh, Elizabeth Wilson, Gene Saks, Gerry Robert Byrne, Jay Patterson, Jerry Mayer, Jessica Tandy, Joe Paparone, 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

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, James Warrior, 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