8 Movies Like Sideways (2004) On Kanopy

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. 

The self destructive, substance abusing history teacher Dan (Ryan Gosling) works in a Brooklyn middle-school and is constantly at odds with the curriculum, preferring to teach 13 year old kids Marxist theory in class. Meanwhile, his student Drey (Shareeka Epps) has to go through struggles of her own, her brother being in jail on drug charges and her single mother having to work long hours to make ends meet. Slowly, an unlikely and tender friendship between teacher and student evolves, in which it becomes less and less clear who of them is the adult part. Steering away from cliches, Half Neslon is not your typical social drama. Its intelligent plot twists, great cast (with outstanding performances by both Gossling and Epps) and slow, non dramatic storytelling makes this a highly underestimated movie that, although treating depressive topics without any easy relief for the viewer, will leave with an inner smile, albeit a sad one.

Genre: Drama

Actor: Adepero Oduye, Anthony Mackie, Collins Pennie, Deborah Rush, Deidre Goodwin, Denis O'Hare, Eleanor Hutchins, Jay O. Sanders, Jeff Lima, Karen Chilton, Katie Nehra, Leslie Eva Glaser, Matt Kerr, Monique Gabriela Curnen, Nathan Corbett, Nicole Vicius, Raymond Anthony Thomas, Ron Cephas Jones, Ryan Gosling, Sebastian Sozzi, Shareeka Epps, Sharon Washington, Starla Benford, Stephanie Bast, Thaddeus Daniels, Tina Holmes, Tristan Mack Wilds

Director: Ryan Fleck

Rating: R

Starring Matthew Broderick and a young Reese Witherspoon as, respectively, Jim McAllister, a high school teacher and Tracy Flick, a notorious 'that girl' in his class. When Tracy decides to run for class president, we see the floodgates open as all sorts of bizarre and insane behavior pours out of the two. Quickly, it becomes clear that Tracy will do nearly anything to win, and as circumstances spiral out of control, madness descends - along with hilarity!

Genre: Comedy, Drama, Romance

Actor: B.J. Tobin, Chris Klein, Colleen Camp, Delaney Driscoll, Frankie Ingrassia, Holmes Osborne, Jason Paige, Jeanine Jackson, Jessica Campbell, John Ponzio, Kaitlin Ferrell, Mark Harelik, Matt Golden, Matt Malloy, Matthew Broderick, Molly Hagan, Nicholas D'Agosto, Phil Reeves, Reese Witherspoon, Rohan Quine

Director: Alexander Payne

Rating: R

A young girl is looking for her father while struggling to care for her family. The film is bleak and slow but great performances from the cast, especially the lead, will keep you engaged throughout. The story has a very real, raw, and natural feeling to it, so natural in fact that at times, you will forget it is a movie. And in many ways, it feels that Winter's Bone is to Jennifer Lawrence what The Believer was to Ryan Gosling, as her performance is nothing short of perfect.

Genre: Drama, Mystery

Actor: Ashlee Thompson, Casey MacLaren, Dale Dickey, Garret Dillahunt, Isaiah Stone, Jennifer Lawrence, John Hawkes, Kevin Breznahan, Lauren Sweetser, Ronnie Hall, Shelley Waggener, Sheryl Lee, Tate Taylor

Director: Debra Granik

Rating: R

Somehow an art house film, horror, and romance all in one, Let the Right One In explores the boundaries of its genres with unprecedented finesse, and offers a stunning alternative for those disappointed with recent vampire love stories. From its haunting minimalist imagery to its incredible score, it is persistently beautiful. The film follows twelve-year-old Oskar and Eli, drawing on numerous aspects of traditional undead lore, and still manages an impressive feat in feeling entirely fresh and devoid of cliche. Those in search of a terrifying movie might need to look elsewhere, but if what you're looking for is simply a great watch, don't pass this one up.

Genre: Drama, Horror

Actor: Anders T. Peedu, Henrik Dahl, Ika Nord, Johan Sömnes, Kåre Hedebrant, Karin Bergquist, Karl-Robert Lindgren, Lina Leandersson, Malin Cederblad, Mikael Rahm, Pale Olofsson, Patrik Rydmark, Per Ragnar, Peter Carlberg, Tom Ljungman

Director: Tomas Alfredson

Rating: R

A residential dispute spirals out of control into full, xenophobia-fueled tragedy in this straightforward and elegantly made film that comes from a now-bygone era of mid-budget dramas for adults. House of Sand and Fog may come off as excessively bleak to viewers today, but it manages to capture a very particular mood of paranoia and distrust common in post-9/11 American cinema. And if nothing else, the film is worth watching for a trio of powerful performances that never resort to overacting: from Iranian actress Shohreh Aghdashloo, English screen legend Ben Kingsley, and an always compelling Jennifer Connelly, who was arguably at the peak of her career in the early 2000s.

Genre: Drama

Actor: Ben Kingsley, Frances Fisher, Jennifer Connelly, Jonathan Ahdout, Kia Jam, Kim Dickens, Navi Rawat, Ron Eldard, Shohreh Aghdashloo

Director: Vadim Perelman

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 documentary about the rise and fall of the Enron Corporation, the energy-trading and utilities conglomerate that gained worldwide attention in 2001 upon its headline-grabbing bankruptcy. Detailing the massive amount of fraud and malfeasance committed by the organization’s top executives, the film delves into the many intricate strategies and "special purpose” entities that were manufactured in order to hide enormous losses and debt from shareholders and the general public. It’s a fascinating and distressing examination of hubris and greed, with so many ethical considerations laid aside in the pursuit of financial gain. The film is as pertinent today as it was when it was released in 2005—perhaps even more so in this post-financial collapse era of increased distrust in corporate agendas.

Genre: Documentary

Actor: Al Kaseweter, Amanda Martin-Brock, Arnold Schwarzenegger, Barbara Boxer, Bethany McLean, Bill Clinton, Carol Coale, David Freeman, Dick Cheney, Gray Davis, Jim Chanos, John Beard, Joseph Dunn, Kevin Phillips, Max Eberts, Peter Coyote, Peter Elkind, Philip Hilder, Reggie Dees II, Tim Belden

Director: Alex Gibney

Rating: Not Rated, R

Shot as a single day, it tells the story of college professor George (Colin Firth) who, unable to cope with the death of his partner months prior, resolves to commit suicide. The movie is not all dark, however, there are moving, deeply human encounters as George moves through his last day. Fashion designer Tom Ford's directorial debut and set in 1960s Los Angeles, it speaks powerfully of the colour-stripping effects of grief and loneliness. Fantastic performance also by Julianne Moore as Charley, an equally lonely and desperate character, but with a markedly different story. A Single Man is a gorgeous film in every sense of the word.

Genre: Drama, Romance

Actor: Aaron Sanders, Adam Shapiro, Colin Firth, Elisabeth Harnois, Erin Daniels, Ginnifer Goodwin, Jenna Gavigan, Jon Hamm, Jon Kortajarena, Julianne Moore, Keri Lynn Pratt, Lee Pace, Matthew Goode, Melissa Goodwin Shepherd, Nicholas Hoult, Nicole Steinwedell, Paul Butler, Paulette Lamori, Ridge Canipe, Ryan Simpkins, Teddy Sears, Tricia Munford

Director: Tom Ford

Rating: R