Best movies like Sideways

Three middle-aged wealthy couples take vacations together in Spring, Summer, Autumn and Winter. Along the way we are treated to mid-life, marital, parental and other crises.

A drop-out from upper-class America picks up work along the way on oil-rigs when his life isn't spent in a squalid succession of bars, motels, and other points of interest.

A wealthy woman from Manhattan's Upper East Side struggles to deal with her new identity and her sexuality after her husband of 16 years leaves her for a younger woman.

Corporate downsizing expert Ryan Bingham spends his life in planes, airports, and hotels, but just as he’s about to reach a milestone of ten million frequent flyer miles, he meets a woman who causes him to rethink his transient life.

Kyle Fisher has one last night to celebrate life as a single man before marrying Laura, so he sets out to Vegas with four of his best buddies. But a drug and alcohol filled night on the town with a stripper who goes all the way, turns into a cold night in the desert with shovels when the stripper goes all the way into a body bag after dying in their bathroom. And that's just the first of the bodies to pile up before Kyle can walk down the aisle...

Jenna is a pregnant, unhappily married waitress in the deep south. She meets a newcomer to her town and falls into an unlikely relationship as a last attempt at happiness.

Married couple Jack and Terry Linden are experiencing a difficult period in their relationship. When Jack decides to step outside the marriage, he becomes involved with Edith, who happens to be the wife of his best friend and colleague, Hank Evans. Learning of their partners' infidelity, Terry and Hank engage in their own extramarital affair together. Now, both marriages and friendships are on the brink of collapse.

A road trip comedy about three friends who travel across the country in a Wiener Wagon to beat up a popular daytime talk show therapist.

Grady is a 50-ish English professor who hasn't had a thing published in years—not since he wrote his award winning 'Great American Novel' 7 years ago. This weekend proves even worse than he could imagine as he finds himself reeling from one misadventure to another in the company of a new wonder boy author.

A recently retired man embarks on a journey to his estranged daughter's wedding, only to discover more about himself and life than he ever expected.

It has been nine years since we last met Jesse and Celine, the French-American couple who once met on a train in Vienna. Now, live in Paris with twin daughters, but have spent a summer in Greece on the invitation of an author colleague of Jesse's. When the vacation is over and Jesse must send his teenage son off to the States, he begins to question his life decisions, and his relationship with Celine is at risk.

A mild-mannered bank executive mentors a teenage con artist and tries to make a career change as a doughnut merchant.

Marcus is a successful advertising executive who woos and beds women almost at will. After a company merger he finds that his new boss, the ravishing Jacqueline, is treating him in exactly the same way. Completely traumatised by this, his work goes badly downhill.

As the devoutly single Don Johnston is dumped by his latest girlfriend, he receives an anonymous pink letter informing him that he has a son who may be looking for him.

Celeste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered businesswoman and budding novelist; he, a free spirit who keeps things from getting boring. Their only problem is that they have decided to get divorced. Can their perfect relationship withstand this minor setback?

Three 40-something women in a small English town meet weekly for a ritual of gin, cigarettes, and sweets -- and swapped stories arguing which of them has the most pathetic love life. Kate is headmistress at the local school; her best friends are the town's police chief and a cynical, thrice-divorced doctor.

A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.

After a rough divorce, Frances, a 35 year old book editor from San Francisco takes a tour of Tuscany at the urgings of her friends. On a whim she buys Bramasole, a run down villa in the Tuscan countryside and begins to piece her life together starting with the villa and finds that life sometimes has unexpected ways of giving her everything she wanted.

An inspirational speaker becomes reinvigorated after meeting a lively woman who shakes up his mundane existence.

Marital infidelity, religion, a guy in heaven wearing a Wizards jersey, anal fetishes, cigarettes and schizophrenia, ghosts, and how it’s going to get worse before it gets better.

Four very different Montreal university teachers gather at a rambling country house to prepare a dinner. Remy (married), Claude (a homosexual), Pierre (involved with a girlfriend) and Alain (a bachelor) discuss sex, the female body and their affairs with them. Meanwhile, their four female guests, Louise (Remy's wife of 15 years), Dominique (a spinster), Diane (a divorcée) and Danielle (Pierre's girlfriend) are spending the time at a downtown health gym. They also discuss sex, the female body and, naturally, men. Later in the evening, they finally meet at the country house and have dinner. A ninth guest, named Mario, who used to know Diane, drops in on the group for some talk and has a surprise of his own.

Eddie, the 40-year-old confirmed bachelor finally says "I do" to the beautiful and sexy Lila. But during their honeymoon in Mexico, the woman of his dreams turns out to be a total nightmare, and the guy who could never pull the trigger realizes he’s jumped the gun.

A newly single New Yorker must re-locate to Florida for her dream job. She drives south with her widowed dad, her mom's ashes in a coffee can, and a GPS with a mind of its own.

A meditation on love and its various incarnations, set within a community of friends in Oregon. It is described as an exploration of the magical, mysterious and sometimes painful incarnations of love.

Exactly one year after Tom meets Violet, he surprises her with a wedding ring. By all accounts, Tom and Violet are destined for their happily ever after. However, this engaged couple just keep getting tripped up on the long walk down the aisle.

Dylan and Jamie think it's going to be easy to add the simple act of sex to their friendship, despite what Hollywood romantic comedies would have them believe. They soon discover however that getting physical really does always lead to complications.

After she quits her lucrative job, Olivia finds herself unsure about her future and her relationships with her successful and wealthy friends.

Andrew returns to his hometown for the funeral of his mother, a journey that reconnects him with past friends. The trip coincides with his decision to stop taking his powerful antidepressants. A chance meeting with Sam - a girl also suffering from various maladies - opens up the possibility of rekindling emotional attachments, confronting his psychologist father, and perhaps beginning a new life.

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.

When his mother dies, a teenager takes a road-trip in a stolen car to find his long-lost brother. Along the way he discovers a profound connection with the car-owner and with himself as well.

A common friend's sudden death brings three men, married with children, to reconsider their lives and ultimately leave together. But mindless enthusiasm for regained freedom will be short-lived.

When Jack and Sally announce that they're splitting up, this comes as a shock to their best friends Gabe and Judy. Maybe mostly because they also are drifting apart and are now being made aware of it. So while Jack and Sally try to go on and meet new people, the marriage of Gabe and Judy gets more and more strained, and they begin to find themselves being attracted to other people.

A group of old friends at a Hens Night discuss their issues, uncertainties, fears and fantasies.

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.

After her boyfriend commits suicide, a young woman attempts to use the unpublished manuscript of a novel and a sum of money he left behind to reinvent her life.

The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

Hard-drinking novelist Zach Hutton spirals out of control after his wife and mistress both leave him. Alone and crippled by a bad case of writer's block, Zach slips in and out of casual relationships and one-night stands, while his drinking becomes more and more severe. With the help of a bartender and his therapist, Zach confronts his demons — women and alcohol.

Professor Lawrence Wetherhold might be imperiously brilliant, monumentally self-possessed and an intellectual giant -- but when it comes to solving the conundrums of love and family, he's as downright flummoxed as the next guy.

A bride's divorced parents find their old feelings for each other during the wedding reception and over the course of the next few days upsetting the newlywed's honeymoon.

While traveling for work in a city far from their homes, a novelist and a corporate accountant find themselves in bed together. Although she’s married, and he’s seeing someone, their intense attraction turns a one-night stand into an unexpected relationship and a respite from the obligations of daily life. Through a series of moments – some profound, some silly, some intensely intimate – we see a portrait of an evolving relationship that could become the most significant one of their lives.

A road trip to Los Angeles inadvertently leads a young man from Wyoming into a wild maze of psychotic hit-men, racy women, jewel thieves and a salsa band.

Wendy is a smart single woman in the big city who’s never been able to find a good job or decent relationship. But when her estranged father dies, Wendy suddenly inherits a beautiful yet struggling Napa Valley winery. With the help of her best friend, Wendy will have to deal with a local winemaker and his father, a shrewd competitor who’s trying to crush her vineyard.

Friends for ten years, a group of twenty-somethings head for the ski slopes as guests of Ian's father. (Ian and dad are estranged because dad worked too many hours when Ian was a lad.) Dad has something to say, but Ian won't listen. Meanwhile, David is gay and virginal; Ian's business partner, Keaton, is unhappy that his sister Jane is pregnant with no plans to tell the father; Lisa is everybody's pal and no one's lover; John, stuck in adolescence, is always on the make. He brings German-born stunner, Carla, and promptly loses her affection to Hans, a fast-talking ski instructor. David meets Manny: they have chess in common. Soon, surprises abound as relationships take new turns.

Quite a bit can happen over the course of a single day in L.A., and when smooth-talking scam artist Johnny decides to throw a bachelor party for his best friend Bill the events of the day take a bizarre turn. As the festivities get underway, the appearance of a transvestite prostitute, a trigger-happy ex-con, and a notorious porn king signal that this isn't going to be a typical night out.

Nathan and Maggie are in the throes of a passionate affair. They're young, good-looking, and both have boyfriends. When Nathan is assigned to write a travel article on romantic hot-spots in Napa Valley, these unconventional lovers test the limits of the sensuality and fantasy that bond them.

A husband and wife reevaluate their marriage after their closest friends, another couple decide to split up after twelve years.

A man and a woman go out on a "big" third date. He's ashamed to admit he just lost his job, and she's afraid he'll run away if he finds out that she has a kid. Small lies lead to bigger ones and the night gets crazy very soon.

A couple endures a series of mishaps right before their wedding day.

After being fired, Rebecca hours back to her old home town to attend her friends wedding on Christmas Eve and visit her mother. But when she tries to return home she finds she must relive Christmas Eve over and over until she gets it right.

A widow struggling to keep the local vineyard and raising her two young boys may be in store for a Christmas miracle when she falls for a big city playboy sent to get intel on a prospective vineyard for sale.