3 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. 

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

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