6 Movies Like Sideways (2004) On Rokuchannel

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. 

, 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: Amitai Marmorstein, Andrea Brooks, Andrew Airlie, Anjelica Huston, Anna Kendrick, Beatrice King, Brent Sheppard, Bryce Dallas Howard, 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

, 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

Monster is a biographical depiction of Aileen Wuornos (Charlize Theron), a prostitute and serial killer who murdered seven men in Florida between 1989 and 1990. The film follows the burgeoning relationship between Wuornos and young Selby Wall (Christina Ricci, in a role based on Wuornos' real-life girlfriend Tyria Moore), as she grows increasingly desperate to provide for her young companion financially. Her desperation and her rage against men, brought on by years of both childhood and adult abuse, leads her down a dark path of murder and theft, even as she struggles to shield Selby from the horror of her crimes. The overwhelming highlight of the film is Theron’s mesmerizing performance as Wuornos—a role that won her a well-deserved Academy Award for Best Actress in 2004. She’s almost unrecognizable and altogether phenomenal as the volatile and increasingly unstable Wuornos, whose ferocity is interwoven with surprising affection for young Selby. This unexpected tenderness lends the film an air of tragic poignancy, and provides a bittersweet portrayal of a severely troubled woman. Very much intended for mature audiences only, Monster is a fascinating recreation of a disturbing yet compelling chapter in the annals of true crime in America.

Genre: Crime, Drama

Actor: Al, Annie Corley, Brett Rice, Bruce Dern, Bubba Baker, Catherine Mangan, Charlize Theron, Christian Stokes, Christina Ricci, Cree Ivey, Glenn R. Wilder, Jesse Stern, Jim R. Coleman, Kaitlin Riley, Kane Hodder, Lee Tergesen, Lyllian Barcaski, Magdalena Manville, Marc Macaulay, Marco St. John, Pruitt Taylor Vince, Romonda Shaver, Rus Blackwell, Scott Wilson, Stephan Jones, Tim Ware

Director: Patty Jenkins

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 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