41 Movies Like Sideways (2004) On Itunes (Page 3)

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. 

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: Aaron Frazier, Aki Aleong, Al Rodrigo, Ashley Edner, Ben Kingsley, Bonita Friedericy, Brian Reed Garvin, Carlos Gómez, Cooper Thornton, Dan Brinkle, David Carrera, Dennison Samaroo, Frances Fisher, Frank Gallegos, Izabella St. James, Jennifer Connelly, Joe Howard, Jonathan Ahdout, Joyce Kurtz, Karl Makinen, Ken Kerman, Kia Jam, Kim Dickens, Marco Rodriguez, Mark Chaet, Matthew Waite, Max Jansen Weinstein, Michael Papajohn, Namrata Singh Gujral, Nasser Faris, Navi Rawat, Pamela Shaddock, Ray Abruzzo, Ron Eldard, Scott Kinworthy, Scott N. Stevens, Shani Rigsbee, Shohreh Aghdashloo, Spencer Garrett, Tom Reynolds, Zoran Radanovich

Director: Vadim Perelman

An extraordinary documentary full of drama, comedy and heartbreak. It follows two penguins, a couple, for a year as they migrate, give birth and face hardships and tragedy. It captures never seen before moments that stand as a perfect illustration of survival in particular and life in general. All in a very well crafted documentary that you will find both instructive and deeply moving. Won the Oscar for Best Documentary Feature.

Genre: Documentary, Family

Actor: Charles Berling, Fiorello, Jules Sitruk, Morgan Freeman, Romane Bohringer

Director: Luc Jacquet

Rating: G

Madeleine (Embeth Davidtz) runs a high-brow art gallery in Chicago and has to take a trip to North Carolina to meet with an artist she wants to sign. She uses this opportunity to also meet her husband’s family, who is originally from there.

She is introduced into the small world of rural North Carolina, personified in Ashley (Amy Adams), the wife of her husband’s brother. Ashley is a wide-eyed but good-hearted person who has never left her town and who is in a bad relationship but pregnant with her first child. 

Ashley is the true main character of this movie (even if all Adams accolades were for ‘best supporting’ awards). Her joyfulness, her pregnancy, and her interactions with Madeliene are studied closely in this subtle but touching family drama.

Genre: Comedy, Drama

Actor: Alessandro Nivola, Alicia Van Couvering, Amy Adams, Ben McKenzie, Bobby Tisdale, Celia Weston, David Kuhn, Embeth Davidtz, Frank Hoyt Taylor, Jerry Minor, Jill Wagner, Joanne Pankow, Matt Besser, R. Keith Harris, Scott Wilson, Will Oldham

Director: Phil Morrison

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

Ryan Bingham (George Clooney) is a corporate axman, he comes in a fires people when the managers are too afraid to do it themselves. The nature of his work requires a lot of flying, short lived meetings in transit zones and he absolutely loves it, and he has a certain goal in mind. When the company tries a new approach to corporate downsizing he has to change his way and view of life. It's full of cynicism and warmth. If you are familiar with Jason Reitman's previous work, you'll feel right at home, if you don't : Get to it!

Genre: Comedy, Drama, Romance

Actor: Adam Rose, Adhir Kalyan, Adrienne Lamping, Amy Morton, Anna Kendrick, Chris Lowell, ​Christopher Lowell, Cut Chemist, Danny McBride, Dave Engfer, George Clooney, J.K. Simmons, Jason Bateman, Jeff Witzke, Jerry Vogel, Matt O'Toole, Melanie Lynskey, Sam Elliott, Steve Eastin, Tamala Jones, Thomas M. Martilotti, Vera Farmiga, Zach Galifianakis

Director: Jason Reitman

Rating: R

The Sessions is drama about Mark O’Brien (John Hawkes), a quadriplegic who is forced to live in an iron lung due to complications from childhood Polio. A poet by trade, Mark longs to experience the touch of a woman, and despite his condition, to ultimately lose his virginity at the age of 38. After consultation with his parish priest (William H. Macy), Mark begins to see a professional sex surrogate (Helen Hunt), who slowly opens his mind and his body to the pleasures of sexuality. A very frank depiction of sex and sensuality, The Sessions is unflinching yet utterly tender storytelling. Hawkes and Hunt are both wonderfully real and honest in their performances. It’s the type of film that will surprise you by the ending at how much it has moved you.

Genre: Comedy, Drama, Romance

Actor: Adam Arkin, Annika Marks, B.J. Clinkscales, Blake Lindsley, Daniel Quinn, Helen Hunt, J. Teddy Garces, James Martinez, Jarrod Bailey, Jennifer Kumiyama, John Hawkes, Jonathan Hanrahan, Ming Lo, Moon Bloodgood, RayVeness, Rhea Perlman, Robin Weigert, Rusty Schwimmer, Tobias Forrest, W. Earl Brown, William H. Macy, Мун Бладгуд

Director: Ben Lewin

Rating: R

In this ensemble cast directed by Wes Anderson, we see a very dysfunctional family with three very unique siblings who grow apart from each other due to their father, a charismatic and ever-absent grifter. However, when he announces his immanent death, the whole family is forced to confront each other, themselves and their childhoods as they gather in their patriarchal home together for the first time in years. An absolutely gorgeously filmed movie, the usage of color, pattern and 60's rock music alone makes it worth seeing, and the beautiful story just sweetens the deal.

Genre: Comedy, Drama

Actor: Al Thompson, Alec Baldwin, Amir Raissi, Andrew Wilson, Anjelica Huston, Ben Stiller, Bill Murray, Brian Smiar, Brian Tenenbaum, Danny Glover, Dipak Pallana, Don McKinnon, Donal Lardner Ward, Ebon Moss-Bachrach, Eric Chase Anderson, Frank Wood, Gary Evans, Gene Hackman, Grant Rosenmeyer, Greg Goossen, Guido Venitucci, Gwyneth Paltrow, Irina Gorovaia, Jennifer Wachtell, Jonah Meyerson, Kalani Queypo, Keith Charles, Kumar Pallana, Larry Pine, Liam Craig, Luke Wilson, Max Faugno, Mel Cannon, Nova Landaeus-Skinnar, Owen Wilson, Pawel Wdowczak, Rex Robbins, Roger Shamas, Rony Clanton, Saidah Arrika Ekulona, Sam Hoffman, Seymour Cassel, Sheelagh Tellerday, Sonam Wangmo, Stephen Dignan, Stephen Lea Sheppard, Tatiana Abbey, Tom Lacy, Wes Anderson, 吉恩·哈克曼

Director: Wes Anderson

Rating: R

The late German actor Ulrich Mühe plays Gerd Wiesler, a merciless Stasi officer who has doubts about the loyalty of a famous playwright (Sebastian Koch) and his wife Christa-Maria (Martina Gedeck) to the communist party. To say he spies on the artist couple is an understatement: in true Stasi fashion, he watches them day and night, listens in on their conservations, reads their mail, and watches them have sex. However, it turns out this was a tad too close, because Wiesler becomes increasingly absorbed in them and is forced to question his obedience as a Stasi officer. In his feature film debut, German director Florian Henckel von Donnersmarck delivers a quietly chilling melodrama on a topic that still affects the lives of many East Germans and was deserving of more attention. It is also a telling piece on the inhumane nature of totalitarianism and the humanity of individuals that are forced to live with it. A special film that will stay with you for a long time.

Genre: Drama, Thriller

Actor: Anabelle D. Munro, Bastian Trost, Charly Hubner, Fabian von Klitzing, Gabi Fleming, Gitta Schweighöfer, Hans-Uwe Bauer, Harald Polzin, Herbert Knaup, Hildegard Schroedter, Hinnerk Schönemann, Hubertus Hartmann, Inga Birkenfeld, Jens Wassermann, Kai Ivo Baulitz, Klaus Münster, Ludwig Blochberger, Marie Gruber, Martin Brambach, Martina Gedeck, Matthias Brenner, Michael Gerber, Paul Faßnacht, Paul Maximilian Schüller, Sebastian Koch, Sheri Hagen, Susanna Kraus, Thomas Arnold, Thomas Thieme, Ulrich Mühe, Ulrich Tukur, Volker Michalowski, Volkmar Kleinert, Werner Daehn

Director: Florian Henckel von Donnersmarck

Rating: R

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, Loretta Lynch, 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