28 Best Movies Like Sideways ...

28 Best Movies Like Sideways ...

If you liked this film , you will probably love these too! In this collection we highlight some of the best films that share a very similar mood to '', and are worth checking out.

1. Friends with Money (2006)

1h 28m Comedy Drama Romance

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

2. Friends & Lovers (1999)

4m Animation Comedy

This action and adventure comedy is drawn in simple appearance and combines cute forest animals with extreme graphic violence. Each episode revolves around the characters enduring accidental events of bloodshed, pain, dismemberment and/or death.

3. Smart People (2008)

1h 35m Comedy Drama Romance

Professor Lawrence Wetherhold (Dennis Quaid) 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.

4. Celeste & Jesse Forever (2012)

1h 31m Comedy Drama Romance

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?

5. Husbands and Wives (1992)

1h 48m Romance Comedy Drama

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.

6. Friends with Kids (2011)

7. The Trip (2010)

30m Comedy

Steve agrees to review six restaurants and takes Rob with him.

8. About Schmidt (2002)

2h 5m Drama Comedy

66-year-old Warren Schmidt is a retired insurance salesman and has no particular plans other than to drive around in the motor home his wife insisted they buy. He's not altogether bitter, but not happy either, as everything his wife does annoys him, and he disapproves of the man his daughter is about to marry. When his wife suddenly dies, he sets out to postpone the imminent marriage of his daughter to a man he doesn't like, while coping with discoveries about his late wife and himself in the process.

9. Up in the Air (2009)

1h 50m Drama Romance

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.

10. The Puffy Chair (2005)

1h 25m Drama Comedy Romance

Josh's life is pretty much in the toilet. He's a failed NYC indie rocker, and a failing booking agent. But he finds the potential of a small victory in a really bad idea. He decides to purchase a 1985 Lazy Boy on eBay, just like the one his dad had when Josh was a kid. He'll drive cross-country for the chair, staying with Emily at his brother's house on the way, and deliver it to his father as a surprise birthday gift. But when Rhett ends up coming along for the ride, it's three people and a giant purple puffy chair in a too-small van... and one of them has to go before the trip's end.

11. The Anniversary Party (2001)

1h 55m Comedy Drama

While celebrating their reconciliation and six years of marriage, the American actress Sally Nash and the British novelist Joe Therrian receive their close friends, some colleagues and their next door neighbors in a party. Under the effect of Ecstasy, revelations are disclosed and relationships deteriorate among the group.

12. Waking Up in Reno (2002)

1h 31m Comedy Romance

Candy and Lonnie Earl are just crazy about each other. The problem: she's married to Roy and he's married to Darlene. So far it's been a secret affair. But that's about to change, because this foursome is driving cross-country and headed for some big surprises.

13. Melvin Goes to Dinner (2003)

1h 23m Comedy Drama Romance

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.

14. Greenberg (2010)

1h 47m Comedy Drama Romance

A New Yorker moves to Los Angeles in order to figure out his life while he housesits for his brother, and he soon sparks with his brother's assistant.

15. Sex and the City (2008)

2h 25m Comedy Drama Romance

A New York writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her.

16. Drinking Buddies (2013)

1h 30m Romance Drama

Weekend trips, office parties, late night conversations, drinking on the job, marriage pressure, biological clocks, holding eye contact a second too long… you know what makes the line between “friends” and “more than friends” really blurry? Beer.

17. Enough Said (2013)

1h 33m Comedy Drama Romance

Eva is a divorced soon-to-be empty-nester wondering about her next act. Then she meets Marianne, the embodiment of her perfect self. Armed with a restored outlook on being middle-aged and single, Eva decides to take a chance on her new love interest Albert — a sweet, funny and like-minded man. But things get complicated when Eva discovers that Albert is in fact the dreaded ex–husband of Marianne...

18. Ten Inch Hero (2007)

1h 37m Comedy Drama Romance

Four friends search for love and happiness while working at a California sandwich shop.

19. Manhattan (1979)

1h 36m Comedy Drama Romance

Manhattan explores how the life of a middle-aged television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.

20. The Last Kiss (2006)

1h 55m Comedy Drama Romance

Michael has a great job, has his 4 best friends, and is in love with a beautiful girl at 30. He loves Jenna but his life seems predictable until someone else enters his life. It seems that everybody's having relationship problems.

21. California Suite (1978)

1h 43m Comedy Drama Romance

The misadventures of four groups of guests at the Beverly Hills Hotel.

22. Chinese Puzzle (2013)

1h 57m Comedy Drama Romance

Xavier is a 40-year-old father of two who still finds life very complicated. When the mother of his children moves to New York, he can't bear them growing up far away from him and so he decides to move there as well.

23. The Wood (1999)

1h 46m Comedy Drama Romance

In the panicky, uncertain hours before his wedding, a groom with prenuptial jitters and his two best friends reminisce about growing up together in the middle-class African-American neighborhood of Inglewood, California. Flashing back to the twenty-something trio's childhood exploits, the memories capture the mood and nostalgia of the '80s era.

24. Your Friends & Neighbors (1998)

1h 40m Drama Comedy

This adult comedy follows six characters, three men and three women from a cross-section of social groups, as they play sexual power games. When an affair fires up between 2 of the married characters, it sparks a chain of consequences for all of them, including one of the wives falling for another woman!

25. Kicking and Screaming (1995)

1h 36m Comedy Drama Romance

After college graduation, Grover's girlfriend Jane tells him she's moving to Prague to study writing. Grover declines to accompany her, deciding instead to move in with several friends, all of whom can't quite work up the inertia to escape their university's pull. Nobody wants to make any big decisions that would radically alter his life, yet none of them wants to end up like Chet, the professional student who tends bar and is in his tenth year of university studies.

26. Barney's Version (2010)

2h 14m Comedy Drama

The picaresque and touching story of the politically incorrect, fully lived life of the impulsive, irascible and fearlessly blunt Barney Panofsky.

27. Shopgirl (2005)

1h 44m Comedy Drama Romance

Mirabelle is a disenchanted salesgirl and aspiring artist who sells gloves and accessories at a department store. She has two men in her life: wealthy divorcée Ray Porter and struggling musician Jeremy. Mirabelle falls in love with the glamorous Ray, and her life takes a magical turn, but eventually she realizes that she must empower herself and make a choice between them.

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