44 Movies Like Sideways (2004)

Staff & contributors

Chasing the feel of watching Sideways ? Here are the movies we recommend you watch after Sideways (2004).

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!

The Station Agent is about loneliness, change and friendship. Sounds corny right? It’s not. The characters are developed, they have their own reasons for the choices they make and nothing feels forced, neither actions or conversations. It’s a small and wonderful movie about a little man that moves out of the city and his comfort zone when his only friend dies, moves to said friend’s old train station and sets his life there. From there on it follows his social interactions with a slew of people, the relationships he forms with them. Oh, and the little man? Peter Dinklage (Tyrion Lannister), who pulls off a great performance, albeit a quiet one.

Directed by David Cronenberg, Eastern Promises is at times brutal—such is the famous Canadian director's trademark—and operates at a fever pitch of grim violence and revenge. Starring a tattooed, ruthless, and terrifying Viggo Mortensen as a very convincing Russian strong-arm gangster as well as Naomi Watts and Vincent Cassel, it features intense psychological drama and a gritty crime story. Midwife Anna (Watts) delivers the baby of a 14-year-old Russian prostitute, who dies while giving birth, and later learns that she was forced into prostitution by the Mafia. To keep this knowledge from seeping out, she gets entangled deeper into London's criminal underbelly, whose various factions and languages are aptly showcased by Cronenberg. Add to all this a smart script and Mortensen's daring performance and you have yourself an intense auteur thriller in signature Cronenberg style.

Told through a series of flashbacks and personal archival footage, Beginners gives us the story of Oliver (Ewan McGregor), a 38-year-old graphic designer from Los Angeles, and his two parents across three timeframes. Oliver has never had a meaningful relationship. Six months after his mother dies, his father, Hal, played by the amazing, Academy Award-winning, and, sadly, late Christopher Plummer, comes out to Oliver. He lives the last days of his life in liberation and, well, gaiety, before protracting terminal cancer. Some months later, Oliver meets Anna at a party, a young French actress (Mélanie Laurent) who is beautiful and warm-hearted, and they start an affair. Through this all, there's Arthur, a Parson Jack Russell. But don't worry. He doesn't talk. Beginners is a beautiful and intricate film about finding love and happiness. It's funny, warm, and sincere. A beautiful movie.

Directed by celebrated artist-turned-filmmaker Julian Schnabel, who won an award in Cannes for it, The Diving Bell and the Butterfly is the true story of the Parisian journalist and fashion editor Jean-Dominique Bauby (Mathieu Amalric), who suffered a devastating stroke at the age of 43. Paralyzed almost completely by what is termed locked-in syndrome, his left eye was the only part of his body that he was still able to move. In a Herculean effort, Bauby learned to blink in an alphabet code that eventually enabled him to communicate. The film alternates between Bauby's interaction with his visitors and caretakers (including painstakingly dictating his memoir, the titular Le Scaphandre et le Papillon) and dream-like fantasies and memories of his life prior to paralysis. The title alludes to this juxtaposition: the diving bell representing his final state of isolation, akin to a deep-sea diver under a bell, and the butterfly as a symbol for his blinking eye and the freedom he has in his mind, dreams, and imagination. Shot from Bauby's perspective, we see what he sees. Be it his divorced but loyal wife and his family visiting him, or his old father, played by Max von Sydow, which is probably the scene in this fascinating movie that will make you lose it and weep like the rest of us.

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.

A very poetic film by Tony Kaye (American History X) about an English Literature teacher (Adrien Brody - "The Pianist") who only works as a substitute in schools which are located in very poor urban areas. The reason behind his choice is that he doesn't want to bond too much with his students and colleagues because he is trying to control his dark emotions about life and the triviality of our existences (although it sounds depressing it is absolutely not). He also takes care of his last family connection, his grandfather, to whom he is very close and who lives in an elderly home. Unsurprisingly, their relationship is very emotional and deep. Every time you think about your existence, your place in the world, your interactions with other people; watch Detachment.

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.
You might have to wipe some sweat from your forehead once you've finished watching this blistering political thriller. It doesn't make any sense to us that this 2006 movie by documentary director Kevin Macdonald made less than 20 million in box office revenue when it came out, but that makes it even more A Good Movie to Watch material. In addition to being thrilling entertainment, it offers insight into an easily overlooked chapter of recent world history and taut moral dilemmas. The dramatization of Giles Foden's novel features two intense performances: James McAvoy plays the sometimes naive (and maybe a bit too enthralled by power) Scottish doctor Nicholas Garrigan, who becomes the personal physician of none other than Ugandan dictator Idi Amin. Nicknamed “The Butcher of Uganda”, Amin is played by Academy Award-winning character actor Forest Whitaker, who perfectly captures his mood-swinging, crazy brutality. He also completely nails his Ugandan-English accent. An amazing watch!

From Steven Spielberg, Munich is the sharp and thrilling depiction of Mossad agents on a mission to avenge the Munich Massacre, the killing of 11 Israeli Olympic team members at the 1972 Summer Olympics. Despite being based on real events, it’s a work of fiction. This allows the film to stand on clear yet nuanced grounds, focusing on the moral dilemmas that may rise for the secret agents and the perpetrators, now targets. The ensemble cast including Daniel Craig and Eric Bana allow Spielberg to deliver the film you can tell he wanted to make. A personal and striking effort.

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.

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.

Once is about a vacuum cleaner/repairman/street musician and a florist in a boy-meets-girl-then-makes-music tale of love, friendship, family, and freaking great music. You can just feel the passion from this simple but charming low-budget movie capturing the chemistry of music making. The film's music will make your skin tingle and hair stand on end. How good is it? In addition to the film winning an Oscar for its music, the Broadway musical version has won 8 Tonys. In short - get ready for a sonic masterpiece!

A thoughtful drama about the financial crisis, Margin Call is gripping. Seriously, even something as convoluted as the 2008 global economic meltdown is not only accessible and understandable, but it's gripping. Margin Call transports you to the heart of Wall Street, both the financial institutions and the street, literally. It is exciting, well-acted and informative. Uh, also: Kevin Spacey.

Will Ferrell plays a well organized IRS agent named Harold Crick who seems to have figured out everything in his life to the dot. Little does he know his life is being run by someone else, a nervous and morbid novelist, famous for ending her works with the death of the main character. As the nature of his life and eventual doom, he decides to lay back and enjoy the ride, breaking all his ingrained and boring habits. While this film is recommended for everyone, Will Ferrel fans, especially, need to watch this to see Will's acting variety.