Movies like Jamie's Wager (2025)
The best movies like Jamie's Wager (2025) are The Family Jewels (1965), Summer '03 (2018) and An Unexpected Christmas (2021). If Jamie's Wager hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSolo Mio (2026)7.5/10 from 317 votes
- NewestSolo Mio (2026)Released 2026
The Family Jewels (1965)
A young heiress must choose between six uncles, one of which is up to no good and out to harm the girl's beloved bodyguard who practically raised her.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSummer '03 (2018)
16-year-old Jamie Winkle and her extended family are left reeling after her calculating grandmother unveils an array of secrets on her deathbed. As her family deals with her grandmother's surprising dying messages, Jamie sets out to make the most of her summer and explores her sexuality.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisAn Unexpected Christmas (2021)
Jamie hasn’t told his family that he and his now ex-girlfriend Emily broke up. After an inopportune run-in with Emily at the train station in his hometown, Jamie convinces her to pretend they’re still a couple to avoid ruining Christmas for his family.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisA Merry Christmas Wish (2022)
Janie, a rising marketing executive living in The Big Apple, returns to her hometown of Woodland Falls when her Great-Uncle Randall passes away. Randall has even arranged for his farmhand, Dylan to help at the event, which is being held in the farm’s sprawling barn. Aware that her Manhattan boyfriend is anxious for her to return to the city so the pair can jet off to a previously planned holiday on the beach, Janie begins to feel an unexpected emotional tug about living life in a more authentic, meaningful way.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisThe Trouble with Angels (1966)
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMe and My Pal (1933)
On the morning of his wedding to oil baron Peter Cucumber's daughter, Ollie receives a jigsaw puzzle from Stan as a wedding gift. The boys soon become absorbed in the puzzle. A taxi driver, butler, policeman and messenger boy join in as well.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Errand Boy (1961)
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty ever finds is that he can cause havoc no matter what he does.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLaggies (2014)
Overeducated and underemployed, 28 year old Megan is in the throes of a quarterlife crisis. Squarely into adulthood with no career prospects, no particular motivation to think about her future and no one to relate to, Megan is comfortable lagging a few steps behind - while her friends check off milestones and celebrate their new grown-up status. When her high-school sweetheart proposes, Megan panics and- given an unexpected opportunity to escape for a week - hides out in the home of her new friend, 16-year old Annika and Annika's world-weary single dad Craig.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisTaking Care of Business (1990)
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Air Up There (1994)
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home movie. But Saleh is the chief's son and has responsibilities at home, since the tribe's land is threatened by a mining company with its own hotshot basketball team.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Half of It (2020)
Shy, straight-A student Ellie is hired by sweet but inarticulate jock Paul, who needs help wooing the most popular girl in school. But their new and unlikely friendship gets tricky when Ellie discovers she has feelings for the same girl.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisP.S. I Love You (2007)
A young widow discovers that her late husband has left her 10 messages intended to help ease her pain and start a new life.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisSecondhand Lions (2003)
The comedic adventures of an introverted boy left on the doorstep of a pair of reluctant, eccentric great-uncles, whose exotic remembrances stir the boy's spirit and re-ignite the men's lives.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisSolo Mio (2026)
After Matt's dreams of a picturesque Italian wedding are shattered when his fiancée leaves him at the altar, he embarks on his planned honeymoon across Italy alone, immersing himself in the country's vibrant culture, food, and beauty, meeting Gia along the way.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisThunder Road (2018)
A police officer faces a personal meltdown following a divorce and the death of his mother.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSchizopolis (1997)
A man works for the unpleasant guru of a Scientology-like movement.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisShanghaied (1915)
A shipowner intends to scuttle his ship on its last voyage to get the insurance money. Charlie, a tramp in love with the owner's daughter, is grabbed by the captain and promises to help him shanghai some seamen. The daughter stows away to follow Charlie. Charlie assists in the galley and attempts to serve food during a gale.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisCarry On Regardless (1961)
After a bunch of no-hopers approaches an employment agency, the anarchy mounts as they do a series of odd jobs, including a chimp's tea party, trying to stay sober at a wine tasting… and demolishing a house.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMy Girl (1991)
Vada Sultenfuss is obsessed with death. Her mother is dead, and her father runs a funeral parlor. She is also in love with her English teacher, and joins a poetry class over the summer just to impress him. Thomas J., her best friend, is "allergic to everything", and sticks with Vada despite her hangups. When Vada's father hires Shelly, and begins to fall for her, things take a turn to the worse...
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Jamie's Wager?
The closest matches to Jamie's Wager are The Family Jewels (1965), Summer '03 (2018) and An Unexpected Christmas (2021). Below are 17 more, each with the reason it matches.
What should I watch after Jamie's Wager?
Start with The Family Jewels (1965), the closest match to Jamie's Wager.
What is the highest-rated movie like Jamie's Wager?
Solo Mio (2026), rated 7.5/10 by 317 TMDB users.
What is the newest movie like Jamie's Wager?
Solo Mio (2026) is the most recent release on this list.
Are there English movies like Jamie's Wager?
Yes: The Family Jewels (1965), Summer '03 (2018) and An Unexpected Christmas (2021).
How are movies similar to Jamie's Wager chosen?
First come films that Trakt’s viewers watch alongside Jamie's Wager, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.