Best movies like Sideways

A unique, carefully handpicked, selection of the best movies like Sideways Starring Fumiyo Kohinata, Katsuhisa Namase, Rinko Kikuchi, Kyoka Suzuki, and more. If you liked Sideways then you may also like: Three Fugitives, The Yellow Handkerchief, Up in Smoke, Vibrator, The Way and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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A struggling writer and his engaged buddy hit the road for California wine country. Remake of the 2004 film 'Sideways'.

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Three Fugitives

On his first day after being released from jail for 14 armed bank robberies, Lucas finds himself caught up in someone else's robbery. Perry has decided to hold up the local bank to raise money so that he can keep his daughter, Meg, and get her the treatment she needs. Dugan, a detective, assumes Lucas helped plan the robbery, and hence Lucas, Perry and Meg become three fugitives.

The Yellow Handkerchief

The story is about a convict released from prison for an old murder who is thinking about returning to his ex-wife and his former life. If she puts a yellow handkerchief on the window, it would mean that she wants him back at home.

Up in Smoke

An unemployed pot-smoking slacker and amateur drummer, Anthony Stoner ditches his strict parents and hits the road, eventually meeting kindred spirit Pedro de Pacas. While the drug-ingesting duo is soon arrested for possession of marijuana, Anthony and Pedro get released on a technicality, allowing them to continue their many misadventures and ultimately compete in a rock band contest, where they perform the raucous tune "Earache My Eye."

Vibrator

Rei is a freelance writer embattled by personal demons. She hears voices in her head, and has sleeping problems, eating disorders and drinks excessively. On Valentine's Day, she meets truck driver Takatoshi. She joins him on a journey in his bumpy and shaky truck - which vibrates in tune with her uneasy soul.

The Way

When his son dies while hiking the famed Camino de Santiago pilgrimage route in the Pyrenees, Tom flies to France to claim the remains. Looking for insights into his estranged child’s life, he decides to complete the 500-mile mountain trek to Spain. Tom soon joins up with other travelers and realizes they’re all searching for something.

Where the Buffalo Roam

Semi-biographical film based on the experiences of gonzo journalist Hunter S. Thompson.

Wild Hogs

Restless and ready for an adventure, four suburban bikers leave the safety of their subdivision and head out on the open road. But complications ensue when they cross paths with an intimidating band of New Mexico bikers known as the Del Fuegos.

On the Road

Dean and Sal are the portrait of the Beat Generation. Their search for "It" results in a fast paced, energetic roller coaster ride with highs and lows throughout the U.S.

Roadside Prophets

Sid and Nancy screenplay author Abbe Wool makes her directorial debut with this tale of a factory worker name Joe (X front man John Doe) who hits the road on his Harley to scatter the ashes of a co-worker. Joined by wannabe biker Sam (Adam Horovitz of the Beastie Boys), Joe journeys from Los Angeles to Nevada, meeting all sorts of characters (played by the likes of David Carradine, John Cusack, Timothy Leary and Arlo Guthrie) along the way.

Johnson Family Vacation

Nate Johnson, a Los Angeles man estranged from his wife and three children, decides to reconnect with his family by taking them with him on a road trip to Missouri for a big family reunion.

Kalifornia

A journalist duo go on a tour of serial killer murder sites with two companions, unaware that one of them is a serial killer himself.

Kill Your Darlings

A desperate young writer is lured on a wild ride through the desert by a mysterious woman in this darkly comic take on the all-American road trip. Along the way they cross paths with a hapless mobster, a 6 foot transvestite and a lovesick housewife, all on the way to their celebrity TV shrink in Las Vegas... Things quickly spiral out of control into a dangerous cat-and-mouse game... a writer's frantic search for inspiration becomes intertwined with a motley crew of quirky characters seeking love and adventure at any cost.

Best Friends

Two young couples taste the "free and easy" life on a cross country motor-home tour until love backfires and tragedy follows.

Coast to Coast

Barnaby and Maxine Pierce, an embattled married couple in Connecticut, are on the verge of divorce. Their son is getting married in California and they decide to drive across the country to attend. Along the way, as they visit family and friends, they reflect on their tattered relationship and the events that transpired to create the estrangement.

Crossroads

Three friends get together and bury a box making a pact to open it at midnight at their high school graduation. In the little town in Georgia that they live in, things soon change. One is little miss perfect, one is an engaged prom queen, and the other is a pregnant outcast. The night of graduation, they open the box and they strike up a conversation. All of a sudden, one brings up the topic of her going to Los Angeles for a record contract audition. They all decide to go together and they leave. With a little money, they set out on the road with a guy named Ben. When one of them tells the other a rumor that he might be a homicidal maniac they are all scared of him. When they reach LA, Lucy falls in love with Ben and against her father's wishes, she stays and she goes to the audition.

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.

Dirty Mary Crazy Larry

Down-on-their-luck racers Larry and Deke steal from a supermarket manager to buy a car that will help them advance their racing chances. Their escape does not go as planned when Larry's one-night stand, Mary, tags along for the ride.

Duct Tape Forever

When an evil land baron's limo falls into a sinkhole outside Possum Lodge, lodge leader Red Green is ordered to pay the baron $10,000 or lose his beloved lodge forever. Red considers various money-making schemes concocted by his buddies, but it's his nerdy nephew Harold who hits on an idea that just might save their wood-smoked bacon: a duct-tape sculpture contest in Minneapolis that offers a $10,000 third-place prize.

Every Which Way but Loose

Philo Beddoe is your regular, easygoing, truck-driving guy. He's also the best bar-room brawler west of the Rockies. And he lives with a 165-pound orangutan named Clyde. Like other guys, Philo finally falls in love - with a flighty singer who leads him on a screwball chase across the American Southwest. Nothing's in the way except a motorcycle gang, and legendary brawler Tank Murdock.

Fathers' Day

A woman cons two old boyfriends into searching for her runaway son by convincing both that they are the boy's father.

Going the Distance

Nick is a successful young man whose comfortable West Coast life couldn't be better. However, when his girlfriend falls under the influence of lecherous music producer Lenny Swackhammer, Nick impulsively decides to travel to Toronto to intervene. Nick's buddies Tyler and Dime opt to turn the quest into a cross-country road trip that's complete with wacky antics and encounters with beautiful women.

Gone

A contemporary psychological thriller in which a young British couple travelling through the Australian outback become involved with a mysterious and charismatic American whose motive for imposing his friendship upon them becomes increasingly suspect and sinister.

Tommy Boy

To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.

Scarecrow

Two drifters bum around, visit earthy women and discuss opening a car wash in Pittsburgh.

Midnight Run

A bounty hunter pursues a former Mafia accountant who embezzled $15 million of mob money. He is also being chased by a rival bounty hunter, the F.B.I., and his old mob boss after jumping bail.

Highwaymen

James Cray watched as his wife was killed by Fargo, a hit-and-run serial murderer. After severely injuring Fargo and going to prison for several years, James is now determined to avenge his wife's death. He drives across the country looking for Fargo's 1972 Cadillac Eldorado, which the now-disabled killer has turned into a rolling death trap. James' search is helped by a state traffic officer and a singer with her own agenda.

The Guilt Trip

An inventor and his mom hit the road together so he can sell his latest invention.

Scorpion

A top counter-intelligence agent thwarts a hijacking and is assigned to protect one of the terrorists who plan to turn evidence over for a plea bargain. Unfortunately, the terrorist organization attacks where the agent is guarding the man, wounding him and killing the agent's best friend. The agent decides to take down the terrorist organization on his own to avenge his friend's death at their hands.

Honeysuckle Rose

Buck Bonham is a country singer on the road caught in a romantic triangle with Dyan Cannon and Amy Irving, the daughter of one of his longtime musical sidekick.

Leaving Normal

Darly, a waitress with a past that's weighing her down, decides to drive to Alaska to try and come to terms with her unfortunate history. Along the way, she meets Marianne, an impulsive young woman leaving an abusive relationship. The two hit the road together and keep driving north, bonding over the hardships that they have endured and meeting a number of eccentric characters as they get closer to their destination.

Lost in America

David and Linda Howard are successful yuppies from LA. When he gets a job disappointment, David convinces Linda that they should quit their jobs, liquidate their assets, and emulate the movie Easy Rider, spending the rest of their lives traveling around America...in a Winnebago.

The Motorcycle Diaries

Based on the journals of Che Guevara, leader of the Cuban Revolution. In his memoirs, Guevara recounts adventures he and best friend Alberto Granado had while crossing South America by motorcycle in the early 1950s.

Take Me Home

In New York City, Thom is broke and jobless, illegally working as a taxi driver. Claire is a successful business-woman, but personally she's in shambles - then comes the phone call that her estranged father is in the hospital. Not knowing what to do, Claire hops in Thom's cab and orders him to just drive and so he does. They find themselves in Pennsylvania and Claire makes the rash decision to drive across the country to California. On the road, there are many detours as the obstacles and secrets force them to learn about themselves and each other.

Thumb Tripping

Gary and Shay are two happy-go-lucky flower children who hitchhike in the beautiful Big Sur-Monterey area of California.

The Trip

When 19-year-old gay-rights activist Tommy and 24-year-old Alan first meet in 1973, they find themselves on the opposite sides of the political coin...

The Trip

When Steve Coogan is asked by The Observer to tour the country's finest restaurants, he envisions it as the perfect getaway with his beautiful girlfriend. But, when she backs out on him, he has no one to accompany him but his best friend and source of eternal aggravation, Rob Brydon.

The Trip to Greece

Steve Coogan and Rob Brydon continue their travelogue series with a visit to Greece.

Zacharia Farted

After finding a mysterious key on an unmarked grave, friends Michael Bates and Brian Moore embark on a cross country road trip to find its owner.

Prince Avalanche

Two highway road workers spend the summer of 1988 away from their city lives. The isolated landscape becomes a place of misadventure as the men find themselves at odds with each other and the women they left behind.

She's In Portland

Two college friends, now in their thirties, admire each others' lives and feel trapped in their own. Wes, tied to a demanding career and responsibilities to family, extends a work trip to drag his dispirited artist friend Luke to find Luke's "one that got away."

Dead by Monday

Dead by Monday is a darkly comic tale of love and death... but not necessarily in that order. Julie is a sweet, vulnerable young woman who lacks confidence and is obsessed with the memory of her dead husband whom she idealizes. Alex is an angry writer. Talented but unable to repeat the success of his first novel, he has nothing left to say. Or live for. He just wants to die. Fate introduces these two lost souls at the edge of a cliff. While picking flowers Julie accidentally falls off. Alex, who has come to blow his brains out, is interrupted by her cry for help, just before he pulls the trigger.

The Collaborators

A tale of two art students who, after a horrific event, are forced to take off across country in a stolen taxi to evade the law.

Cab to Canada

Fact-based story about a Pasadena cab driver who picks up what he believes is a routine fare, an elderly woman on her way to a funeral. However, the wealthy woman is soon is insisting that the cabbie drive her on a cross-country trip that ends up entailing 3100 miles and ending in Vancouver. Initially contentious, the two eventually find a reluctant friendship growing.

The Long Dumb Road

Two guys serendipitously meet at a time when they both find themselves at personal crossroads and decide to embark on an unplanned road trip across the American Southwest.

Amerikana

Peter and Chris, two young American friends in their late 20s, go from South Dakota to California on a scooter, and as they travel across the American landscape they see their country through different eyes, ranging from Peter's cynically nihilistic point of view, to Chris' high expectations and romantic notions of the United States.

No Place Like Home

When Susan, a film producer from NYC, goes to Jamaica to shoot a shampoo commercial, she finds herself, through a series of unforeseen circumstances, drifting further and further away from the world she knows and into the life of the island, a strange alternative reality that turns many of her previously held assumptions upside down.

The Big One

Anna has just buried her beloved aunt as California waits once more for the big quake to hit. Unsure of where she is going, she climbs into her old convertible for a trip through the desert. Along the way she meets a series of bizarre characters, including two dancing glitter girls, a crazy jogger and a heartbreaking crooner. Anna's friends and family also appear repeatedly to her in her car for imaginary conversations. The levels of time and perception, of the past and present, begin to merge and the trip increasingly becomes a journey into Anna's consciousness.

The Three Undelivered Letters

Noriko had been engaged to marry Toshiyuki Fujimura, who worked at her father’s bank. One day however, Fujimura mysteriously disappears. From that day, Noriko keeps herself locked up in her room. After three years of Noriko shutting herself up like a doll without a soul, Fujimura suddenly returns. Noriko’s family’s first reaction was strong rejection, but Noriko asks no questions and embraces him warmly. One day, as Noriko is cleaning her husband’s room, three envelopes accidentally fall from the pages of one of the books she had picked up. The first letter is dated August 11th, saying that his wife had suddenly taken ill. The second, dated August 20th, says that his wife is now critically sick, and the third letter, dated September 1st, is an announcement of his wife’s death. The wife is obviously Noriko, but she is alive and well. Do the letters then mean a preliminary notice of Noriko’s death?

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