4 Movies Like Sideways (2004) On Hulu

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, 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, 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, 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

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

Starring a sad-sack Steve Carrell and an ensemble cast with brilliant timing and real heart, Little Miss Sunshine is a rare understated comedy that brings laughter and tears. As a dysfunctional family's youngest member gets chosen to be in a pageant in California, the family must come together and support her through her journey. Along the path that they take, they learn and cope with each other. A great movie filled with phenomenal acting and writing with a real heart that will leave you breathless.

Genre: Comedy, Drama

Actor: Abigail Breslin, Alan Arkin, Beth Grant, Brenda Canela, Bryan Cranston, Dean Norris, Geoff Meed, Gordon Thomson, Greg Kinnear, Jerry Giles, Jill Talley, Joan Scheckel, John Walcutt, Julio Oscar Mechoso, Justin Shilton, Lauren Shiohama, Marc Turtletaub, Mary Lynn Rajskub, Matt Winston, Mel Rodriguez, Paul Dano, Paula Newsome, Steve Carell, Steven Christopher Parker, Terry Bolo, Toni Collette, Wallace Langham

Director: Jonathan Dayton, Valerie Faris

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, Andrew Weissmann, Arnold Schwarzenegger, Barbara Boxer, Bethany McLean, Bill Clinton, Carol Coale, David Freeman, Dick Cheney, Gray Davis, Henry Waxman, 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