46 Movies Like Sideways (2004)

Staff & contributors

Chasing the feel of watching Sideways ? Here are the movies we recommend you watch right after.

Best friends Miles and Jack are off to wine country to celebrate Jack's last week of freedom before he gets married. They drop white lies about themselves, with Miles pretending to be a successful writer and Jack not mentioning his impending wedding, and soon meet two beautiful women whom they spend the rest of their stay with. What sounds like a dreamy bachelor's celebration, however, soon unravels into a messy tangle of tall tales. Miles and Jack contemplate their situation in smart, sad, and silly turns, delivering excellent performances and an overall hard-hitting road movie. 

In 2008, legendary and controversial director Darren Aronofsky delivered yet another unforgettable allegory, starring Mickey Rourke as Randy "The Ram" Robinson, an aging professional wrestler long past his prime, who is struggling to retain a sense of identity, purpose, and dignity later in life. Rourke, who worked as a professional boxer in his 90s and, like his protagonist, almost hung his hat at the time the movie was shot, delivers a once-in-a-lifetime performance that rightly earned him a Golden Globe. Everybody talked about this movie when it came out! Marisa Tomei's performance, who plays the mid-40s stripper The Ram pursues a serious relationship with, was also deemed iconic by some critics. Shot on 16mm film, The Wrestler's cinematography, like its acting, feels incredibly raw, intimate, and realistic. It is essentially about bouncing back, making amends, and growing old and features acting performances that will be remembered for a long time. One for the books!

Genre: Drama, Romance

Actor: Abraham Aronofsky, Ajay Naidu, Alex Whybrow, Alyssa Bresnahan, Andrea Langi, Armin Amiri, Ben Van Bergen, Bernadette Penotti, Bill Walters, Brandon DiCamillo, Brian Heffron, Charlotte Aronofsky, Claudio Castagnoli, Cobian, Daniel Healy Solwold Jr., Daniel Solwold Jr., Darnell Kittrell, Donnetta Lavinia Grays, Douglas Crosby, Dustin Howard, Dylan Keith Summers, Dylan Summers, E.J. Carroll, Emmanuel Yarborough, Eric Santamaria, Erika Smith, Ernest Miller, Evan Rachel Wood, Felice Choi, Giovanni Roselli, Gregg Bello, Jamar Shipman, Jeff Chena, Jen Cohn, Jess Liaudin, John Corson, John D'Leo, John Zandig, Jon Trosky, Judah Friedlander, Lloyd Anoa'i, Marcia Jean Kurtz, Marisa Tomei, Mark Margolis, Matt Cannon, Michael Drayer, Mickey Rourke, Mike Miller, Nate Hatred, Nicholas K. Berk, Nick Papagerio, Olivia Baseman, Paul E. Normous, Paul Thornton, Peter Conboy, Rebecca Darke, Rob Strauss, Robert D. Siegel, Robert Oppel, Ron Killings, Ryan Lynn, Ryan Tygh, Sakinah Bingham, Scott Franklin, Steven Haworth, Sylvia Kauders, Todd Barry, Tommy Farra, Vernon Campbell, Wass Stevens

Director: Darren Aronofsky

Rating: R

The Station Agent is about loneliness, change and friendship. Sounds corny right? It’s not. The characters are developed, they have their own reasons for the choices they make and nothing feels forced, neither actions or conversations. It’s a small and wonderful movie about a little man that moves out of the city and his comfort zone when his only friend dies, moves to said friend’s old train station and sets his life there. From there on it follows his social interactions with a slew of people, the relationships he forms with them. Oh, and the little man? Peter Dinklage (Tyrion Lannister), who pulls off a great performance, albeit a quiet one.

Genre: Comedy, Drama

Actor: Bobby Cannavale, Ileen Getz, Jase Blankfort, Jayce Bartok, Jeremy Bergman, Joe Lo Truglio, John Slattery, Josh Pais, Lynn Cohen, Maile Flanagan, Marla Sucharetza, Michelle Williams, Patricia Clarkson, Paul Benjamin, Paula Garces, Peter Dinklage, Raven Goodwin, Richard Kind

Director: Tom McCarthy

Rating: R

Directed by David Cronenberg, Eastern Promises is at times brutal—such is the famous Canadian director's trademark—and operates at a fever pitch of grim violence and revenge. Starring a tattooed, ruthless, and terrifying Viggo Mortensen as a very convincing Russian strong-arm gangster as well as Naomi Watts and Vincent Cassel, it features intense psychological drama and a gritty crime story. Midwife Anna (Watts) delivers the baby of a 14-year-old Russian prostitute, who dies while giving birth, and later learns that she was forced into prostitution by the Mafia. To keep this knowledge from seeping out, she gets entangled deeper into London's criminal underbelly, whose various factions and languages are aptly showcased by Cronenberg. Add to all this a smart script and Mortensen's daring performance and you have yourself an intense auteur thriller in signature Cronenberg style.

Genre: Crime, Drama, Mystery, Thriller

Actor: Aleksandar Mikic, Aleksander Mikic, Alice Henley, Armin Mueller-Stahl, David Papava, Donald Sumpter, Elisa Lasowski, Jerzy Skolimowski, Josef Altin, Mina E. Mina, Naomi Watts, Raza Jaffrey, Sarah-Jeanne Labrosse, Sinead Cusack, Tamer Hassan, Tatiana Maslany, Tereza Srbová, Tony Cook, Viggo Mortensen, Vincent Cassel

Director: David Cronenberg

Rating: R

Told through a series of flashbacks and personal archival footage, Beginners gives us the story of Oliver (Ewan McGregor), a 38-year-old graphic designer from Los Angeles, and his two parents across three timeframes. Oliver has never had a meaningful relationship. Six months after his mother dies, his father, Hal, played by the amazing, Academy Award-winning, and, sadly, late Christopher Plummer, comes out to Oliver. He lives the last days of his life in liberation and, well, gaiety, before protracting terminal cancer. Some months later, Oliver meets Anna at a party, a young French actress (Mélanie Laurent) who is beautiful and warm-hearted, and they start an affair. Through this all, there's Arthur, a Parson Jack Russell. But don't worry. He doesn't talk. Beginners is a beautiful and intricate film about finding love and happiness. It's funny, warm, and sincere. A beautiful movie.

Genre: Comedy, Drama, Romance

Actor: AlgeRita Wynn, Algerita Wynn Lewis, Amanda Payton, Bambadjan Bamba, Bruce French, Catherine McGoohan, China Shavers, Christopher Plummer, Cosmo, Ewan McGregor, Goran Visnjic, Jennifer Hasty, Joanna Trzepiecinska, Jodi Long, Jose Yenque, Kai Lennox, Keegan Boos, Lana Young, Lou Taylor Pucci, Luke Diliberto, Mélanie Laurent, Maria Semotiuk, Mary Page Keller, Mélanie Laurent, Melissa Tang, Michael Chieffo, Patrick Birkett, Patryk Wisniewski, Rafael J. Noble, Reynaldo Pacheco, Rodney Saulsberry, Terry Walters, Tymon Tymanski

Director: Mike Mills

Rating: N/A, R

Directed by celebrated artist-turned-filmmaker Julian Schnabel, who won an award in Cannes for it, The Diving Bell and the Butterfly is the true story of the Parisian journalist and fashion editor Jean-Dominique Bauby (Mathieu Amalric), who suffered a devastating stroke at the age of 43. Paralyzed almost completely by what is termed locked-in syndrome, his left eye was the only part of his body that he was still able to move. In a Herculean effort, Bauby learned to blink in an alphabet code that eventually enabled him to communicate. The film alternates between Bauby's interaction with his visitors and caretakers (including painstakingly dictating his memoir, the titular Le Scaphandre et le Papillon) and dream-like fantasies and memories of his life prior to paralysis. The title alludes to this juxtaposition: the diving bell representing his final state of isolation, akin to a deep-sea diver under a bell, and the butterfly as a symbol for his blinking eye and the freedom he has in his mind, dreams, and imagination. Shot from Bauby's perspective, we see what he sees. Be it his divorced but loyal wife and his family visiting him, or his old father, played by Max von Sydow, which is probably the scene in this fascinating movie that will make you lose it and weep like the rest of us.

Genre: Drama, History

Actor: Agathe de La Fontaine, Anne Alvaro, Anne Consigny, Emma de Caunes, Emmanuelle Seigner, Fiorella Campanella, Françoise Lebrun, Gérard Watkins, Isaach De Bankolé, Jean-Philippe Écoffey, Jean-Pierre Cassel, Laure de Clermont-Tonnerre, Lenny Kravitz, Marie-Josée Croze, Marina Hands, Mathieu Amalric, Max von Sydow, Michael Wincott, Nicolas Le Riche, Niels Arestrup, Olatz Lopez Garmendia, Patrick Chesnais, Talina Boyaci, Zinedine Soualem

Director: Julian Schnabel

Rating: PG-13

You know you're in for a treat when you see Julia Louis-Dreyfus and James Gandolfini heading the cast of a sweet and slightly goofy comedy. Steadily going beyond his persona in The Sopranos, you see James Gandolfini playing a role that his fans have probably always imagined him playing: a nice, funny guy with an endearing personality. Directed by Nicole Holofcener, Enough Said almost has a sit-com feel to it: a divorced single parent and masseuse, Eva (Louis-Dreyfus), is looked up by a guy, she briefly met at a party, Albert (Gandolfini). Upon finding out they have much in common, the two start dating. At the same time, she meets Marianne (Catherine Keener), who she becomes friends with and who cannot stop talking ill of her apparently awful ex-husband. You guessed it: it's her new, promising date, Albert. Things get muddy and very funny as she starts to doubt, whether she has made a big mistake. Hilarious, romantic, and smart, it's very much like we expected: a real treat.

Genre: Comedy, Drama, Romance

Actor: Amy Landecker, Anjelah Johnson-Reyes, Barry Jenner, Ben Falcone, Catherine Keener, Christopher Nicholas Smith, Eve Hewson, James Gandolfini, Jessica St. Clair, Julia Louis-Dreyfus, Kathleen Rose Perkins, Lennie Loftin, Luke Grakal, Michaela Watkins, Phillip Brock, Rebecca Drysdale, Rick Irwin, Rob Mayes, Rob Steiner, Sarah Burns, Tavi Gevinson, Toby Huss, Toni Collette, Tracey Fairaway

Director: Nicole Holofcener

Rating: PG-13

A very poetic film by Tony Kaye (American History X) about an English Literature teacher (Adrien Brody - "The Pianist") who only works as a substitute in schools which are located in very poor urban areas. The reason behind his choice is that he doesn't want to bond too much with his students and colleagues because he is trying to control his dark emotions about life and the triviality of our existences (although it sounds depressing it is absolutely not). He also takes care of his last family connection, his grandfather, to whom he is very close and who lives in an elderly home. Unsurprisingly, their relationship is very emotional and deep. Every time you think about your existence, your place in the world, your interactions with other people; watch Detachment.

Genre: Drama

Actor: Adrien Brody, Betty Kaye, Blythe Danner, Bryan Cranston, Celia Au, Chris Papavasiliou, Christina Hendricks, Isiah Whitlock Jr., James Caan, Josh Pais, Louis Zorich, Lucy Liu, Marcia Gay Harden, Mary Joy, Patricia Rae, Ralph Rodriguez, Reagan Leonard, Ronen Rubinstein, Samantha Logan, Sami Gaye, Sami Gayle, Tim Blake Nelson, William Petersen

Director: Tony Kaye

Rating: Not Rated

, 2011

It might seem like a no-brainer that trying to make a comedy movie featuring a character with cancer is not a great idea. And while there may be a good share of failed attempts in that category, 50/50 is not one of them. And then it might come as a surprise that this subtle attempt at cancer comedy comes courtesy of Superbad creators Seth Rogen and Evan Goldberg. It also stars indie cutie Joseph Gordon-Levitt as the young and fit Adam Lerner, who works as a writer for public radio before learning that he has malignant tumors all along his spine. Between his overbearing mum (Anjelica Huston), slightly obnoxious but good-hearted bestie (Seth Rogen), self-help groups, and his therapist (played by Anna Kendrick), he struggles to find a way of acquiescing to his 50/50 chance of survival. Similarly, 50/50 strikes a delicate balance between the bromance gags, the date-movie elements, and the grave subject matter at its heart. It manages to mine humor, pathos, and simple honesty from a dark situation, and is not afraid to “go there”. The result is truly compassionate comedy.

Genre: Comedy, Drama

Actor: Adrian Glynn McMorran, Amitai Marmorstein, Andrea Brooks, Andrew Airlie, Anjelica Huston, Anna Kendrick, Beatrice King, Brent Sheppard, Bryce Dallas Howard, Cameron K. Smith, Chilton Crane, Christopher De-Schuster, D.C. Douglas, Daniel Bacon, Donna Yamamoto, Jason Vaisvila, Jessica Parker Kennedy, Jonathan Levine, Joseph Gordon-Levitt, Laura Bertram, Lauren Miller, Luisa D'Oliveira, Marie Avgeropoulos, Matt Frewer, Matty Finochio, P. Lynn Johnson, Peter Kelamis, Philip Baker Hall, Sarah Smyth, Serge Houde, Seth Rogen, Stephanie Belding, Stephen Colbert, Sugar Lyn Beard, Tom MacNeill, Veena Sood, Will Reiser, William 'Big Sleeps' Stewart, Yee Jee Tso

Director: Jonathan Levine

Rating: R

You might have to wipe some sweat from your forehead once you've finished watching this blistering political thriller. It doesn't make any sense to us that this 2006 movie by documentary director Kevin Macdonald made less than 20 million in box office revenue when it came out, but that makes it even more A Good Movie to Watch material. In addition to being thrilling entertainment, it offers insight into an easily overlooked chapter of recent world history and taut moral dilemmas. The dramatization of Giles Foden's novel features two intense performances: James McAvoy plays the sometimes naive (and maybe a bit too enthralled by power) Scottish doctor Nicholas Garrigan, who becomes the personal physician of none other than Ugandan dictator Idi Amin. Nicknamed “The Butcher of Uganda”, Amin is played by Academy Award-winning character actor Forest Whitaker, who perfectly captures his mood-swinging, crazy brutality. He also completely nails his Ugandan-English accent. An amazing watch!

Genre: Drama

Actor: Abby Mukiibi Nkaaga, Adam Kotz, Barbara Rafferty, David Ashton, David Oyelowo, Devon Diep, Dick Stockley, Forest Whitaker, Giles Foden, Gillian Anderson, James McAvoy, Kerry Washington, Martina Amati, Sam Okelo, Simon McBurney, Stephen Rwangyezi

Director: Kevin Macdonald

Rating: R

From Steven Spielberg, Munich is the sharp and thrilling depiction of Mossad agents on a mission to avenge the Munich Massacre, the killing of 11 Israeli Olympic team members at the 1972 Summer Olympics. Despite being based on real events, it’s a work of fiction. This allows the film to stand on clear yet nuanced grounds, focusing on the moral dilemmas that may rise for the secret agents and the perpetrators, now targets. The ensemble cast including Daniel Craig and Eric Bana allow Spielberg to deliver the film you can tell he wanted to make. A personal and striking effort.

Genre: Action, Drama, History, Mystery, Thriller

Actor: Abdelhafid Metalsi, Alexander Beyer, Ami Weinberg, Amos Lavi, Amrou Al-Kadhi, Andreas Lust, Arturo Arribas, Ayelet Zurer, Baya Belal, Ben Youcef, Bijan Daneshmand, Brian Goodman, Carim Messalti, Charley Gilleran, Ciarán Hinds, Daniel Bess, Daniel Craig, David A. Hamade, Dianne Zaremba, Djemel Barek, Eric Bana, Faruk Pruti, Félicité Du Jeu, Geoffrey Rush, Gila Almagor, Guri Weinberg, Guy Amir, Hagit Dasberg, Hanns Zischler, Hiam Abbass, Hicham Nazzal, Hichem Yacoubi, Hisham Suliman, Igal Naor, Jalil Naciri, Jim McKay, Jonathan Avigdori, Jonathan Uziel, Joram Voelklein, Karim Saidi, Karim Saleh, Kevin Collins, Laurence Février, Lili Bordán, Liron Levo, Lisa Werlinder, Lyes Salem, Lynn Cohen, Mahmoud Zemmouri, María Casal, Marie-Josée Croze, Marie-Josée Croze, Martin Ontrop, Mathieu Amalric, Mathieu Kassovitz, Mehdi Nebbou, Meret Becker, Merik Tadros, Michael Lonsdale, Michael Schenk, Mihalis Giannatos, Moa Khouas, Moritz Bleibtreu, Moshe Ivgy, Mostefa Djadjam, Mouna Soualem, Mousa Kraish, Nasser Memarzia, Ohad Knoller, Omar Metwally, Omar Mostafa, Ori Pfeffer, Ossie Beck, Patrick Kennedy, Rad Lazar, Raffi Tavor, Renana Raz, Richard Brake, Rim Turki, Robert John Burke, Sabi Dorr, Saïda Bekkouche, Sam Feuer, Sami Samir, Sarah Mennell, Sasha Spielberg, Sharon Alexander, Shmuel Edelman, Souad Amidou, Stéphane Freiss, Steven Spielberg, Tom Wlaschiha, Ula Tabari, Valeria Bruni Tedeschi, Valeria Bruni‑Tedeschi, Wojciech Machnicki, Yehuda Levi, Yvan Attal

Director: Steven Spielberg

Rating: R

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

Nebraska is a poem distilled into a film. Peter Travers from Rolling Stone says "is it a comedy or a drama? Both at the same time, as life itself." Everything about it is perfect: the acting, the photography, the story. In case that's not enough and you need to know the plot to get convinced, I'll tell you that it's a road movie about a senile old man and his son. If you still want more information, you can Google it, but come on! You'll just be wasting time that would be better spent on watching this masterpiece.

Genre: Adventure, Drama

Actor: Angela McEwan, Anthony G. Schmidt, Bob Nelson, Bob Odenkirk, Bruce Dern, Devin Ratray, Franklin Dennis Jones, June Squibb, Mary Louise Wilson, Missy Doty, Rance Howard, Stacy Keach, Tim Driscoll, Will Forte

Director: Alexander Payne

Rating: R

, 2007

Once is about a vacuum cleaner/repairman/street musician and a florist in a boy-meets-girl-then-makes-music tale of love, friendship, family, and freaking great music. You can just feel the passion from this simple but charming low-budget movie capturing the chemistry of music making. The film's music will make your skin tingle and hair stand on end. How good is it? In addition to the film winning an Oscar for its music, the Broadway musical version has won 8 Tonys. In short - get ready for a sonic masterpiece!

Genre: Drama, Music, Romance

Actor: Darren Healy, Geoff Minogue, Gerard Hendrick, Glen Hansard, Hugh Walsh, Mal Whyte, Marcella Plunkett, Markéta Irglová

Director: John Carney

Rating: R

A thoughtful drama about the financial crisis, Margin Call is gripping. Seriously, even something as convoluted as the 2008 global economic meltdown is not only accessible and understandable, but it's gripping. Margin Call transports you to the heart of Wall Street, both the financial institutions and the street, literally. It is exciting, well-acted and informative. Uh, also: Kevin Spacey.

Genre: Drama, Thriller

Actor: Aasif Mandvi, Al Sapienza, Ashley Williams, Demi Moore, Grace Gummer, Jeremy Irons, Jimmy Palumbo, Kevin Spacey, Maria Dizzia, Mary McDonnell, Oberon K.A. Adjepong, Paul Bettany, Penn Badgley, Peter Y. Kim, Simon Baker, Stanley Tucci, Susan Blackwell, Zachary Quinto

Director: J. C. Chandor

Rating: R

Kimberly Peirce's first–out of only three—film was a smashing success, mostly due to her dedication to the subject matter. Peirce spent years researching the life and tragic death of Brandon Teena after reading an article about him in The Village Voice. She felt a particular kind of kinship as a queer person herself, and wanted to construct a story out of real facts that would put the spotlight on love and the desire for connection, and not that much on the violence which dominated the public discourse. In Falls City, Nebraska, the director conducted interviews with Lana Tisdale (Brandon's girlfriend) and her mother, while attending the ongoing trial. She took years to cast the lead and from hundreds of cis women, lesbians, and trans people, she chose the unknown actress Hilary Swank, who went on to win the Best Actress Academy Award (and the irony of that is not lost on us). The film features fantastic performances aplenty and very raw storytelling, visualized by neorealist style and low lighting. Direct references were the films of Martin Scorcese and John Cassavetes, but Boys Don't Cry has its own blend of beauty and cruelty to take pride in.

Genre: Crime, Drama

Actor: Alicia Goranson, Alison Folland, Brendan Sexton III, Caitlin Wehrle, Cheyenne Rushing, Chloe Sevigny, Craig Erickson, Gabriel Horn, Gail Cronauer, Guilford Adams, Hilary Swank, Jackson D. Kane, Jeannetta Arnette, Jerry Haynes, Josh Ridgway, Libby Villari, Lisa Renee Wilson, Lou Perryman, Matt McGrath, Paige Carl Griggs, Peter Sarsgaard, Rob Campbell, Robert Prentiss, Shana McClendon

Director: Kimberly Peirce

Rating: R