
Sideways
Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.
Movies Like Sideways
Similar in style, tone, and themes — find your next watch.

Playing It Cool
2014★ 5.8
A young man meets and instantly falls in love with an engaged woman.

Looking: The Movie
2016★ 7.1
Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

Sacramento
2025★ 6.3
When free-spirited Rickey suddenly reappears in father-to-be Glenn’s life, the two former best friends embark on a spontaneous road trip from LA to Sacramento.

Factotum
2005★ 6.2
This drama centers on Hank Chinaski, the fictional alter-ego of "Factotum" author Charles Bukowski, who wanders around Los Angeles, CA trying to live off jobs which don't interfere with his primary interest, which is writing. Along the way, he fends off the distractions offered by women, drinking and gambling.

The Sisters Brothers
2018★ 6.8
Oregon, 1851. Hermann Kermit Warm, a chemist and aspiring gold prospector, keeps a profitable secret that the Commodore wants to know, so he sends the Sisters brothers, two notorious assassins, to capture him on his way to California.

Tom Jones
1963★ 5.9
Tom loves Sophie and Sophie loves Tom. But Tom and Sophie are of differering classes. Can they find a way through the mayhem to be true to love?

Best Sellers
2021★ 6.4
A cranky, retired author reluctantly embarks on a final book tour to help out a young publisher.

Beautiful Boy
2018★ 7.5
After he and his first wife separate, journalist David Sheff struggles to help their teenage son, who goes from experimenting with drugs to becoming devastatingly addicted to methamphetamine.

The Sure Thing
1985★ 6.5
Gib, a beer-guzzling slob, and Alison, an uptight Ivy-Leaguer, are an unlikely duo stuck together on a cross-country trip during Christmas break. At first they get on each other's nerves but, as time passes, they find their divergent natures complement each other. Now they need to realize what they've already found before it's too late.

The Big Picture
1989★ 5.9
Hollywood beckons for recent film school grad Nick Chapman, who is out to capitalize on the momentum from his national award-winning student film. Studio executive Allen Habel seduces Nick with a dream deal to make his first feature, but once production gets rolling, corporate reality begins to intervene: Nick is unable to control a series of compromises to his high-minded vision, and it's all he can do to maintain his integrity in the midst of filmmaking chaos.

Youth in Revolt
2009★ 6.2
As a fan of Albert Camus and Jean-Luc Godard, teenage Nick Twisp is definitely out of his element when his mother and her boyfriend move the family to a trailer park. When a pretty neighbor named Sheeni plays records by French crooners, it's love at first sight for frustrated and inexperienced Nick. Learning that she is dating someone, Nick launches a hilarious quest to find his way into Sheeni's heart -- and bed.

Murphy's Romance
1985★ 6.2
Emma, a divorced single mother seeking to start her life over, moves to a small town in Arizona. She befriends Murphy, the older local pharmacist, but things turn complicated when her ex-husband shows up.

Inherent Vice
2014★ 6.5
In Los Angeles at the turn of the 1970s, drug-fueled detective Larry "Doc" Sportello investigates the disappearance of an ex-girlfriend.

Fast Times at Ridgemont High
1982★ 6.8
Based on the real-life adventures chronicled by Cameron Crowe, Fast Times follows a group of high school students growing up in Southern California. Stacy Hamilton and Mark Ratner are looking for love, and are helped along by their older classmates, Linda Barrett and Mike Damone. Jeff Spicoli, a perpetually stoned surfer faces-off with the resolute teacher, Mr. Hand. Hilarity and heartbreak ensue.

Broken English
2007★ 5.9
Nora Wilder is freaking out. Everyone around her is either in a relationship, married, or has children, while she's in her thirties, alone with job she's outgrown and a mother who constantly reminds her of it all. Not to mention her best friend Audrey's "perfect marriage". But after a series of disastrous dates, Nora unexpectedly meets Julien, a quirky Frenchman who opens her eyes to a lot more than love.

Less Than Zero
1987★ 6.4
A college freshman returns to Los Angeles for Christmas at his ex-girlfriend's request, but discovers that his former best friend has an out-of-control drug habit.

A Nice Girl Like You
2020★ 5.8
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.

Topper
1937★ 6.7
Madcap couple George and Marion Kerby are killed in an automobile accident. They return as ghosts to try and liven up the regimented lifestyle of their friend and bank president, Cosmo Topper. When Topper starts to live it up, it strains relations with his stuffy wife.

Mrs. Parker and the Vicious Circle
1994★ 5.9
Dorothy Parker remembers the heyday of the Algonquin Round Table, a circle of friends whose barbed wit, like hers, was fueled by alcohol and flirted with despair.

The Clique
2008★ 5.9
A young girl tries to fit in with a clique of popular middle school girls after moving into the guest house of one of their homes.