5 Movies Like Sideways (2004) On Amazon Prime

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

In this comedy/drama, Bill Murray plays an aged, dispirited war veteran named Vincent who openly disdains most people and gives little attention to anything beyond alcohol and horse racing. Living a life of solitude in Brooklyn, everything takes a turn when a young single mother (Melissa McCarthy) and her son Oliver move in next door. Vincent eventually takes on the responsibility of watching over Oliver when Maggie is at work. Murray is perfectly unpleasant in his darkly comedic role, as his relationship with Oliver evolves despite his own misgivings, providing young Oliver (Jaeden Lieberher) with the fatherly/grandfatherly presence he desperately needs. Though somewhat formulaic, St. Vincent rises above expectations by way of great dialogue, favourable performances from all of the leads, and an unbelievably touching finale that will melt your heart. Much better than you probably expect—definitely check this one out.

Genre: Comedy, Drama

Actor: Alexandra Fong, Amber Clayton, Ann Dowd, Bill Murray, Brenda Wehle, Brian Berrebbi, Chris O'Dowd, Chris O'Dowd, Dario Barosso, David Iacono, Deirdre OConnell, Donna Mitchell, Elliot Santiago, Frank Wood, Greta Lee, Jaeden Lieberher, Jaeden Martell, James Andrew O'Connor, Jeff Bowser, Josh Elliott Pickel, Katharina Damm, Kerry Flanagan, Kimberly Quinn, Lenny Venito, Maria Elena Ramirez, Maria-Christina Oliveras, Melanie Nicholls-King, Melissa McCarthy, Naomi Watts, Nate Corddry, Niles Fitch, Orlagh Cassidy, Portia, Ray Iannicelli, Reg E. Cathey, Ron McLarty, Scott Adsit, Terrence Howard, Tim Wilson

Director: Theodore Melfi

Rating: PG-13

From a 1926 play to the iconic 1975 stage musical to Rob Marshall's 2002 extravaganza, Chicag0 has had a strong hold on popular culture. In a way, it's existed almost as long as cinema itself and its transformation across mediums and modes of expression has been well documented. The film carries all the marks of its theatrical predecessors, the expansive sets, the luscious costumes, the sleek characters whose banter and songs alike testify to their great chemistry — there's a lot to admire in such a self-referential spectacle. A black-comedy-fuelled musical about corruption and deceit set during the Jazz Age, Chicago fulfils all its promises. With a stellar ensemble cast featuring Renée Zellweger, Catherine Zeta-Jones, Richard Gere, and John C. Reily, in tandem with dazzling camerawork and most exquisite chiaroscuro lighting, this one brings the stage to the movies. I mean it in the best possible way!

Genre: Comedy, Crime, Drama

Actor: Blake McGrath, Brendan Wall, Bruce Beaton, Catherine Zeta-Jones, Chita Rivera, Christine Baranski, Cliff Saunders, Colm Feore, Conrad Dunn, Cynthia Onrubia, Deidre Goodwin, Deirdre Goodwin, Denise Faye, Dominic West, Ekaterina Chtchelkanova, Eve Crawford, Faye Rauw, Gregory Mitchell, Jayne Eastwood, Jeff Clarke, Jeff Pustil, John C. Reilly, Jonathan Whittaker, Joseph Scoren, Karen Holness, Karine Plantadit, Kathryn Zenna, Ken Ard, Laura Dean, Lucy Liu, Marty Moreau, Michelle Johnston, Monique Ganderton, Mya, Nicki Richards, Paul Becker, Queen Latifah, Renée Zellweger, Rhonda Roberts, Richard Gere, Rick Negron, Rob Smith, Robbie Rox, Robert Montano, Roman Podhora, Sara Ramirez, Sean McCann, Sean Palmer, Sebastian La Cause, Sheri Godfrey, Susan Misner, Taye Diggs, Vicky Lambert

Director: Rob Marshall

Rating: PG-13

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