Movies like Winter Passing (2006)
The best movies like Winter Passing (2006) are Wonder Boys (2000), Sideways (2004) and The Savages (2007). If Winter Passing hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Royal Tenenbaums (2001)7.5/10 from 5,278 votes
- NewestKangaroo Island (2025)Released 2025
Wonder Boys (2000)
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.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisSideways (2004)
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 One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.
Why it matches: Fans watch both · both comedy & drama
Worth the HypeMovies like thisThe Savages (2007)
A sister and brother face the realities of familial responsibility as they begin to care for their ailing father.
Why it matches: Fans watch both · both drama & comedy
Popcorn FlickMovies like thisJunebug (2005)
On the way to meet with an independent artist in the South, newlywed art dealer Madeleine is convinced by her husband, George, that they should stop to meet his family in North Carolina. Madeleine's affluent lifestyle clashes with the family, but she befriends George's wide-eyed and pregnant sister-in-law, Ashley, who is nearing her due date. Through the family, Madeleine gains greater insight into George's character.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisThe Good Life (2007)
A movie about the travails of Jason (Mark Webber), a young gas station attendant and movie projectionist living in Nebraska. His encounters with various social difficulties and with Frances (Zooey Deschanel), a beautiful and enigmatic young woman leads to dramatic changes and decisions in his life.
Why it matches: Fans watch both · both drama & comedy
Away We Go (2009)
Verona and Burt have moved to Colorado to be close to Burt's parents but, with Verona expecting their first child, Burt's parents inexplicably 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.
Why it matches: Fans watch both · both drama & comedy
Popcorn FlickMovies like thisMargot at the Wedding (2007)
Margot Zeller is a short story writer with a sharp wit and an even sharper tongue. On the eve of her estranged sister Pauline's wedding to unemployed musician/artist/depressive Malcolm at the family seaside home, Margot shows up unexpectedly to rekindle the sisterly bond and offer her own brand of support. What ensues is a nakedly honest and subversively funny look at family dynamics.
Why it matches: Fans watch both · both comedy & drama
SnoozefestMovies like thisWaitress (2007)
A small town waitress stuck in a lousy marriage finds love when an exciting out-of-towner enters her life.
Why it matches: Fans watch both · both drama & comedy
Popcorn FlickMovies like thisThe Station Agent (2003)
When his only friend dies, a man born with dwarfism moves to rural New Jersey to live a life of solitude, only to meet a chatty hot dog vendor and a woman dealing with her own personal loss.
Why it matches: Fans watch both · both drama & comedy
Worth the HypeMovies like thisThe Upside of Anger (2005)
After her husband runs off with his secretary, Terry Wolfmeyer is left to fend for herself -- and her four daughters. As she hits rock bottom, Terry finds a friend and drinking buddy in next-door neighbor Denny, a former baseball player. As the two grow closer, and her daughters increasingly rely on Denny, Terry starts to have reservations about where their relationship is headed.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisSunshine Cleaning (2009)
A single mother and her slacker sister find an unexpected way to turn their lives around in this off-beat dramatic comedy. In order to raise the tuition to send her young son to private school the mom starts an unusual business – a biohazard removal/crime scene clean-up service.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisWhile We're Young (2015)
An uptight documentary filmmaker and his wife find their lives loosened up a bit after befriending a free-spirited younger couple.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisThe Descendants (2011)
With his wife Elizabeth on life support after a boating accident, Hawaiian land baron Matt King takes his daughters on a trip from Oahu to Kauai to confront a young real estate broker, who was having an affair with Elizabeth before her misfortune.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisPostcards from the Edge (1990)
A substance-addicted actress tries to look on the bright side even as she's forced to move back in with her mother to avoid unemployment.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisThe Squid and the Whale (2005)
Based on the true childhood experiences of Noah Baumbach and his brother, The Squid and the Whale tells the touching story of two young boys dealing with their parents' divorce in Brooklyn in the 1980s.
Why it matches: Fans watch both · both comedy & drama
Worth the HypeMovies like thisPrivate Life (2018)
Richard and Rachel, a couple in the throes of infertility, try to maintain their marriage as they descend deeper and deeper into the insular world of assisted reproduction and domestic adoption.
Why it matches: Fans watch both · both drama & comedy
Popcorn FlickMovies like thisBroken Flowers (2005)
An introverted man receives an anonymous letter from an ex-lover informing him that he has a son who may be looking for him. A freelance sleuth neighbor motivates the man to embark on a cross-country search for his past flames, seeking answers.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisWhere the Heart Is (1990)
A wealthy businessman shows his young adult kids how tough life can be.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisThe Kids Are All Right (2010)
Two women, Nic and Jules, brought a son and daughter into the world through artificial insemination. When one of their children reaches age, both kids go behind their mothers' backs to meet with the donor. Life becomes so much more interesting when the father, two mothers and children start to become attached to each other.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisPlease Give (2010)
In New York City, a husband and wife butt heads with the granddaughters of the elderly woman who lives in the apartment the couple owns.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisThe Good House (2021)
When wry New England realtor Hildy Good rekindles a romance with her old high-school flame, Frank Getchell, it ignites long-buried emotions and family secrets that propel Hildy toward a reckoning with the one person she's been avoiding for decades: herself. Based on the best-selling novel by Ann Leary.
Why it matches: Fans watch both · both drama & comedy
Popcorn FlickMovies like thisThe Royal Tenenbaums (2001)
Royal Tenenbaum and his wife Etheline had three children and then they separated. All three children are extraordinary --- all geniuses. Virtually all memory of the brilliance of the young Tenenbaums was subsequently erased by two decades of betrayal, failure, and disaster. Most of this was generally considered to be their father's fault. "The Royal Tenenbaums" is the story of the family's sudden, unexpected reunion one recent winter.
Why it matches: Fans watch both · both comedy & drama
Worth the HypeMovies like thisKangaroo Island (2025)
Lou Wells has hit rock bottom after a promising start to her Hollywood career. Now broke and aimless, she reluctantly accepts a plane ticket from her estranged father, Rory to return home to South Australia’s ruggedly beautiful Kangaroo Island. As years of unresolved tension start to resurface, the reunion turns even more complicated when Lou and her sister Freya learn about Rory’s secret.
Why it matches: Fans watch both · both drama & comedy
The Terminal (2004)
An Eastern European tourist unexpectedly finds himself stranded in JFK airport, and must take up temporary residence there.
Why it matches: Fans watch both · both comedy & drama
Worth the HypeMovies like thisEnough Said (2013)
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...
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisGarden State (2004)
Andrew returns to his hometown for his mother’s funeral, a journey that reconnects him with old friends. The trip coincides with his decision to stop taking his powerful antidepressants. A chance meeting with Sam—a girl also struggling with various maladies—opens up the possibility of rekindling emotional connections, confronting his psychologist father, and perhaps beginning a new life.
Why it matches: Fans watch both · both comedy & drama
Worth the HypeMovies like thisMy One and Only (2009)
A mother takes her two sons on an unusual road trip from New York to Pittsburgh, St. Louis and eventually Hollywood in her quest to find a man to take care of them all.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisEllie Parker (2005)
Ellie Parker, an aspiring actress from Australia, lives a hectic Hollywood lifestyle, perpetually trying to land the role that will elevate her career. Living with her lothario musician boyfriend, Justin, Ellie is far from happy, finding support primarily from her friend Sam. But when Ellie meets Chris after a minor traffic accident, she sees new potential for both romance and her life in general.
Why it matches: Fans watch both · both comedy & drama
SnoozefestMovies like thisBarney's Version (2010)
The picaresque and touching story of the politically incorrect, fully lived life of the impulsive, irascible and fearlessly blunt Barney Panofsky.
Why it matches: Fans watch both · both comedy & drama
Worth the HypeMovies like thisThe Cake Eaters (2007)
The death of the Kimbrough family matriarch affects the three male survivors of the clan. Widower Easy tries to reconnect with his old flame, Marg. Eldest son and struggling musician Guy moves back to town, feeling guilty that he missed the funeral. His brother, Beagle, who was his mother's caretaker, falls for Marg's granddaughter, Georgia, a chronically ill girl who fears her time is growing short.
Why it matches: Fans watch both · both drama
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Frequently asked questions
What are the best movies like Winter Passing?
The closest matches to Winter Passing are Wonder Boys (2000), Sideways (2004) and The Savages (2007). Below are 27 more, each with the reason it matches.
What should I watch after Winter Passing?
People who watched Winter Passing most often go on to Wonder Boys (2000), Sideways (2004) and The Savages (2007).
What is the highest-rated movie like Winter Passing?
The Royal Tenenbaums (2001), rated 7.5/10 by 5,278 TMDB users.
What is the newest movie like Winter Passing?
Kangaroo Island (2025) is the most recent release on this list.
Are there English movies like Winter Passing?
Yes: Wonder Boys (2000), Sideways (2004) and The Savages (2007).
How are movies similar to Winter Passing chosen?
First come films that Trakt’s viewers watch alongside Winter Passing, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.