8 Movies Like Sideways (2004) On Hoopla

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. 

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

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

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

Michael Douglas plays Grady Tripp, a craggy, lovable English professor struggling to finish the follow-up to a very successful first novel. It has taken him 7 years, and it's an obvious metaphor for his ridiculous life. The character navigates various tragicomic dilemmas with a stellar supporting cast including Frances McDormand, Tobey Maguire, and Katie Holmes. His editor is Robert Downey Jr. and his nemesis is Rip Torn. Bob Dylan wrote the theme song. How do you not love this movie? It's one of those films that feels like a warm, cozy house (despite the fact that it takes place in a Pittsburgh winter), and it's a great blend of humor and drama.

Genre: Comedy, Drama

Actor: Alan Tudyk, Bingo O'Malley, Charis Michelsen, Elisabeth Granli, Frances McDormand, George Grizzard, James Ellroy, James Kisicki, Jane Adams, John W. Iwanonkiw, Katie Holmes, Kelly Bishop, Michael Cavadias, Michael Douglas, Philip Bosco, Richard Knox, Richard Thomas, Rip Torn, Rob McElhenney, Robert Downey Jr., Sean King, Tobey Maguire, Victor Quinaz, Yusuf Gatewood

Director: Curtis Hanson

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

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, James Warrior, 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, 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