Most Similar Movies to Sideways (2004)
If you are looking for movies like Sideways (2004), you might like movies tagged with keyword : comedy, drama, romance, midlife crisis, road movie, friendship, american film, independent film, california, marriage, self-discovery, life crisis, humor, satire, novel adaptation, academy awards, golden globe, growth, life turning point, wine .
The Upside of Anger (2005), No Pay, Nudity (2016), The Climb (2019), As Good as It Gets (1997), Barney's Version (2010), The Hollars (2016), Funny People (2009) ... Let's take a look at the following list...

The Upside of Anger (2005)
When her husband unexpectedly disappears, a sharp-witted suburban wife and her daughters juggle their mom's romantic dilemmas and family dynamics.
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No Pay, Nudity (2016)
Aging actor Lester Rosenthal (Gabriel Byrne), who has lost his way with his career, with his family, and with his friends (Nathan Lane, Frances Conroy, & Boyd Gaines) finds out that the way out is through.
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The Climb (2019)
Two lifelong pals test the boundaries of their friendship when a woman comes between them.
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As Good as It Gets (1997)
A single mother and waitress, a misanthropic author, and a gay artist form an unlikely friendship after the artist is assaulted in a robbery.
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Barney's Version (2010)
The picaresque and touching story of the politically incorrect, fully lived life of the impulsive, irascible and fearlessly blunt Barney Panofsky.
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The Hollars (2016)
A man returns to his small hometown after learning that his mother has fallen ill and is about to undergo surgery.
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Funny People (2009)
When seasoned comedian George Simmons learns of his terminal, inoperable health condition, his desire to form a genuine friendship causes him to take a relatively green performer under his wing as his opening act.
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The Marriage of a Young Stockbroker (1971)
A stock-broker is stuck in a dreary job and a marriage that's become a dull routine. To cope with the boredom and frustration, he resorts to voyeurism and extramarital love affairs.
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The Best Man (1998)
A pretty Italian (Ines Sastre) weds a wealthy businessman (Dario Cantarelli) while pledging herself to his best man (Diego Abatantuono).
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I'm Reed Fish (2007)
As he is about to be married to the sweetheart of his small town, Reed Fish's (Jay Baruchel) life turns upside down with an old flame's return.
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Change of Plans (2009)
Friends attending a dinner party act like a dysfunctional family.
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Committed (2000)
Determined to save her marriage, a woman (Heather Graham) drives 2,000 miles to find her husband (Luke Wilson) and win him back.
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The Grand Role (2004)
Through archival footage and dramatic readings of his personal writings, the life of Nazi Germany's Propaganda Minister, Josef Goebbels, is examined.
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Husbands (1970)
After the death of a common friend, three married men leave their lives together, seeking pleasure and freedom and ultimately leaving for London.
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Look Both Ways (2005)
During one unusually hot and tragic weekend, four people struggle after hearing some life-changing news, this in turn brings them together.
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The Four Seasons (1981)
Three couples vacation together every season. After one divorces, feelings of betrayal and more spawn criticisms of each other. But the things that keep them together are stronger than those which otherwise might pull them apart.
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Chaos Theory (2008)
The story of an obsessively organized efficiency expert whose life unravels in unexpected ways when fate forces him to explore the serendipitous nature of love and forgiveness.
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