20 best movies like Sideways (2004)

Having suffered a tragedy, Ben becomes a caregiver to earn money. His first client, Trevor, is a hilarious 18-year-old with muscular dystrophy. One paralyzed emotionally, one paralyzed physically, Ben and Trevor hit the road on a trip into the western states. The folks they collect along the way will help them test their skills for surviving outside their calculated existence. Together, they come to understand the importance of hope and the necessity of true friendship.

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.

As an asteroid nears Earth, a man finds himself alone after his wife leaves in a panic. He decides to take a road trip to reunite with his high school sweetheart. Accompanying him is a neighbor who inadvertently puts a wrench in his plan.

Jake and Kristy Briggs are newlyweds. Being young, they are perhaps a bit unprepared for the full reality of marriage and all that it (and their parents) expect from them. Do they want babies? Their parents certainly want them to. Is married life all that there is? Things certainly aren't helped by Jake's friend Davis, who always seems to turn up just in time to put a spanner in the works.

After spending two decades in England, Bill Bryson returns to the U.S., where he decides the best way to connect with his homeland is to hike the Appalachian Trail with one of his oldest friends.

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.

Wondering what has happened to herself, now feeling stagnant and in a rut, Shirley Valentine finds herself regularly talking to the wall while preparing her husband's chips and egg. When her best friend wins a trip-for-two to Greece Shirley begins to see the world, and herself, in a different light.

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?

Cheated on, mistreated and stepped on, the women are holding their breath, waiting for the elusive "good man" to break a string of less-than-stellar lovers. Friends and confidants Vannah, Bernie, Glo and Robin talk it all out, determined to find a better way to breathe.

Greg is coasting through senior year of high school as anonymously as possible, avoiding social interactions like the plague while secretly making spirited, bizarre films with Earl, his only friend. But both his anonymity and friendship threaten to unravel when his mother forces him to befriend a classmate with leukemia.

Rachel is a food writer at a New York magazine who meets Washington columnist Mark at a wedding and ends up falling in love with him despite her reservations about marriage. They buy a house, have a daughter, and Rachel thinks they are living happily ever after until she discovers that Mark is having an affair while she is waddling around with a second pregnancy.

Verona and Burt have moved to Colorado to be close to Burt's parents but, with Veronica expecting their first child, Burt's parents decide to move to Belgium, now leaving them in a place they hate and without a support structure in place. They set off on a whirlwind tour of of disparate locations where they have friends or relatives, sampling not only different cities and climates but also different families. Along the way they realize that the journey is less about discovering where they want to live and more about figuring out what type of parents they want to be.

Harry is a retired teacher in his 70s living in the Upper West Side of New York City where his late wife and he raised his children--where he's lived all his life. When the building he lives in is torn down to make way for a parking garage, Harry and his beloved cat Tonto begin a journey across the United States, visiting his children, seeing a world he never seemed to have the time to see before, making new friends, and saying goodbye to old friends.

In an updated contemporary version of the beloved stage play and 1989 film, "Steel Magnolias" chronicles the lives and friendship of six women in Louisiana. Supporting each other through their triumphs and tragedies, they congregate at Truvy’s beauty shop to ponder the mysteries of life and death, husbands and children - and hair and nails - all the important topics that truly unite and celebrate women.

After a rough divoce, 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.

Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.

Set in 1890s North Wales over a long, hot August weekend, the Victorian calm of a household is suddenly upset with the arrival of a London couple who impose their city ways and thoughts on the more rurally based family. An adaptation of Anton Chekhov's play, "Uncle Vanya."

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.

Magali, forty-something, is a winemaker and a widow: she loves her work but feels lonely. Her friends Rosine and Isabelle both want secretly to find a husband for Magali.

Matt falls for Casey, the new girl in school. She's fun-loving and eccentric, but there's a darkness to her whimsy that Matt can't begin to comprehend. When Casey attempts to commit suicide, her parents place her in a mental institution. Matt springs her out, and together the young lovers head on a road trip. They believe their love can "cure" Casey's problems. Matt starts to wonder, though, if are they inspired or misguided.

Sissy Hankshaw is born with enormous thumbs that help her hitchhiking through the US from a young age. She becomes a model in advertising and her NY agent 'the Countess' sends her to his ranch in CA to shoot a commercial, set against the background of mating whooping cranes. There, she befriends Bonanza Jellybean, one of the cowgirls at the beauty- ranch.

A young widow discovers that her late husband has left her 10 messages intended to help ease her pain and start a new life.

After breaking up with her girlfriend, a nightclub singer, Jane, answers a personal ad from Robin, a real estate agent with AIDS, seeking a cross-country travel partner. On their journey from New York City to Los Angeles, the two stop by Pittsburgh to pick up Robin's friend Holly, who is trying to escape an abusive relationship. With three distinct personalities, the women must overcome their differences to help one another.

30 years after the first film, Oscar and Felix embark on a road trip together, to attend the wedding of Oscar's son to Felix's daughter.

A comedy-drama about best friends - one a straight woman, Abbie, the other a gay man, Robert - who decide to have a child together. Five years later, Abbie falls in love with a straight man and wants to move away with her and Robert's little boy Sam, and a nasty custody battle ensues.

In New York, a struggling actress and a successful writer sing about their failed marriage from two perspectives.

Nora Wilder (Parker Posey), a single, career woman works at a Manhattan boutique hotel where her excellent skills in guest relations lack in the romantic department. If it is not her loving and dominant mother (Gena Rowlands) attempting to set her up that consistently fail, she has her friend’s (Drea de Matteo) disastrous blind dates to rely on as a backup for further dismay. She's surrounded by friends who are all happily engaged or romantically involved and somehow, love escapes Nora -- until she meets an unusual Frenchman (Melvil Poupaud) who helps her discover life beyond her self-imposed boundaries.

In his funky California beach enclave, Chip's the go-to guy for personal insights. But he isn't quite as enlightened when it comes to his own baggage.

A broken family finds their relationships to one another changed by a new arrival in the household.

Amy, a naive college graduate who believes she's destined to be a great poet, begrudgingly accepts a job at a sex shop while she pursues a mentorship with reclusive writer Rat Billings.

Whilst on a short weekend getaway, Louise shoots a man who had tried to rape Thelma. Due to the incriminating circumstances, they make a run for it and thus a cross country chase ensues for the two fugitives. Along the way, both women rediscover the strength of their friendship and surprising aspects of their personalities and self-strengths in the trying times.

With a new iPhone, an apartment near the Grove, and a comfortable bank account left to her by her beloved late husband, Marnie Minervini has happily relocated from New Jersey to Los Angeles to be near her daughter Lori, a successful (but still single) screenwriter, and smother her with motherly love. But when the dozens of texts, unexpected visits, and conversations dominated by unsolicited advice force Lori to draw strict personal boundaries, Marnie finds ways to channel her eternal optimism and forceful generosity to change the lives of others - as well as her own - and find a new purpose in life.

Four actors go to a cabin in the woods to write, direct, and act in a film that will jump-start their careers. Their idea is a horror film about a man with a bag over his head, but what happens when that man mysteriously shows up?

At a picturesque lakeside estate, a love triangle unfolds between the legendary diva Irina, her lover Boris, and the ingénue Nina.

Soon-to-be-wed graduate student Finn Dodd develops cold feet when she suspects her fiancé is cheating on her. In order to clear her head, Finn visits her grandmother, Hy, and great aunt, Glady Joe Cleary, in Grasse, Calif. There, Finn learns that Hy and Glady Joe are members of a group of passionate quilters, and over the course of her visit she is regaled with tales of love and life by women who have collected rich experiences and much wisdom.

Seven close friends reunite for the wedding of two of their friends. Problems arise because the bride and the maid of honor have had a long rivalry over the groom.

In the seventies Strange Fruit were it. They lived the rock lifestyle to the max, groupies, drugs, internal tension and an ex front man dead from an overdose. Even their demise was glamorous; when lightning struck the stage during an outdoor festival. 20 years on and these former rock gods they have now sunk deep into obscurity when the idea of a reunion tour is lodged in the head of Tony, former keyboard player of the Fruits. Tony sets out to find his former bandmates with the help of former manager Karen to see if they can recapture the magic and give themselves a second chance.

Waxing nostalgic about the bittersweet passage from childhood to puberty in this tender coming-of-age tale, four childhood girlfriends -- Teeny, Chrissy, Samantha and Roberta -- recall the magical summer of 1970. During their walk down memory lane, they reconcile experiences with boys, secrets, bullies and more.

A young man with Tourette's Syndrome embarks on a road trip with his recently-deceased mother's ashes.

A 17 year old finds out that his girlfriend is dying, so he sets out to give her an entire life, in the last year she has left.

A group of childhood friends, now in their thirties, reunite at Camp Tamakwa. Only a few of the original campers show up, but they still have a good time reminiscing. The people share experiences and grow while at the camp. They are dismayed to discover that the camp's owner, Unca Lou, is going to close the camp down.

Iris invites her friend Jack to stay at her family's island getaway after the death of his brother. At their remote cabin, Jack's drunken encounter with Hannah, Iris' sister, kicks off a revealing stretch of days.

A 29-year-old lawyer and her lesbian best friend experience a dramatic shift in their longtime bond after one enters a serious relationship

The story revolves around three soldiers — Colee, T.K. and Cheaver — who return from the Iraq War after suffering injuries and learn that life has moved on without them. They end up on an unexpected road trip across the U.S.

Tracy, a lonely college freshman in New York, is rescued from her solitude by her soon-to-be stepsister Brooke, an adventurous gal about town who entangles her in alluringly mad schemes. Mistress America is a comedy about dream-chasing, score-settling, makeshift families, and cat-stealing.

David Portnoy, a 15-year-old birding fanatic, thinks that he's made the discovery of a lifetime. So, on the eve of his father's remarriage, he escapes on an epic road trip with his best friends to solidify their place in birding history.

Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

A trio of beautiful girls set out to revolutionize life at a grungy American university: the dynamic leader Violet Wister, principled Rose and sexy Heather. They welcome transfer student Lily into their group which seeks to help severely depressed students with a program of good hygiene and musical dance numbers.

A clinically depressed teenager gets a new start after he checks himself into an adult psychiatric ward.

Publishing assistant Brett Eisenberg wants to be a big-time editor. However, she lacks self-confidence, a problem that isn't helped by her new, overbearing boss. Brett soon enters into a relationship with Archie, an older man who has plenty of his own issues, including alcoholism, diabetes and a difficult relationship with his daughter. Intent on helping Archie get past his problems, she turns to her dying father for advice.