Movies like Sweepstake Annie (1935)
The best movies like Sweepstake Annie (1935) are Taking Care of Business (1990), 29th Street (1991) and Easy Money (1983). If Sweepstake Annie hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Sweepstake Annie
Quick picks
- Highest ratedLouis C.K.: Hilarious (2010)7.8/10 from 321 votes
- NewestSpa Weekend (2026)Released 2026
Taking 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 · both comedy
Popcorn FlickMovies like this29th Street (1991)
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisEasy Money (1983)
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCa$h (2010)
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a tumultuous adventure through the streets of Chicago, each are pulled deeper and deeper into a desperate spiral of deception and violence – all in the name of money.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Wedding Year (2019)
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisMuch Ado About Nothing (2013)
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSpa Weekend (2026)
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break, the women escape to a luxury spa retreat for an unforgettable weekend dedicated to fun, laughter, and a lot of really bad decisions.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJackass Presents: Bad Grandpa (2013)
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisEenie Meanie (2025)
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Oh My God (2013)
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for writing on his acclaimed show on FX, Louie. Performed in the round in front of a live audience, he discusses such topics as the food chain, animals, divorce, strange anecdotes, broken morality, murder and mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisLouis C.K.: Ridiculous (2026)
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJerry Seinfeld: 23 Hours to Kill (2020)
Jerry Seinfeld takes the stage in New York and tackles talking vs. texting, bad buffets vs. so-called "great" restaurants and the magic of Pop Tarts.
Why it matches: Recommended by TMDB viewers · both comedy
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 · both comedy
Popcorn FlickMovies like thisFun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBabes (2024)
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisIliza Shlesinger: Confirmed Kills (2016)
The standup sensation tackle's TV's "Shark Tank," what it means to be a woman and how to deal with the lawless party goblin that lives in us all.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Hilarious (2010)
In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJimmy O. Yang: Good Deal (2020)
In his debut standup special, Good Deal, Jimmy will tell you all about his take on Asian representation, how he learned to speak English from rap videos, dating tall women, and pursuing his dreams only to disappoint his old school Chinese parents. From assimilation to representation, Jimmy O. Yang delivers an absolutely hilarious hour of comedy in Good Deal.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisPunch-Drunk Love (2002)
A socially awkward and volatile small business owner meets the love of his life after being threatened by a gang of scammers.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisBet Your Life (1948)
Against his wishes, Leon Errol is forced to buy a sweepstakes ticket
Why it matches: Similar story and style · both comedy
The Gay Deception (1935)
A wide-eyed working girl wins a $5,000 sweepstakes and plunges into the lush life of New York City, where she meets a bellboy who is more than he seems.
Why it matches: Similar story and style · both comedy
Lucky Partners (1940)
Two strangers split a sweepstake prize to go on a fake honeymoon with predictable results.
Why it matches: Similar story and style · both comedy
Call It Luck (1934)
A London taxicab driver cashes in on a big sweepstakes ticket and becomes the prey of a confidence-gang that sells him a nag of a cavalry horse on the claim that it is a brother to a current Derby winner.
Why it matches: Similar story and style · both comedy
Olive's $weep$take Ticket (1941)
Olive gets a phone call that she has won first prize in a sweepstake. After a frantic search, she locates her ticket, only to have it blow out the window. Help, Popeye!
Why it matches: Similar story and style · both comedy
Sudden Money (1939)
Promises of happier times dawn for the financially distressed Patterson family when father Sweeney and brother-in-law Archibald "Doc" Finney win a $150,000 grand prize in the sweepstake contest. With their windfall, each member of the family decides to pursue a dream.
Why it matches: Similar story and style · both comedy
Winona (2020)
Seems like an ordinary trip to a remote beach. Four young women enjoy the warmth of the sun, the coolness of the sea and one another's company. None of them is "Winona"
Why it matches: Similar story and style · both comedy
Head or Tails (2016)
Lilly convinces her best friend René to join her on a nocturnal trespassing adventure. The two young women break into a zoo and enter an idiosyncratic animal kingdom where the boundaries between fear and desire begin to blur.
Why it matches: Similar story and style · both comedy
Night on Earth (1991)
A quintet of cabbies in five cities and their remarkable fares on the same eventful night.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this
Like Sweepstake Annie and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Sweepstake Annie?
The closest matches to Sweepstake Annie are Taking Care of Business (1990), 29th Street (1991) and Easy Money (1983). Below are 27 more, each with the reason it matches.
What should I watch after Sweepstake Annie?
Start with Taking Care of Business (1990), the closest match to Sweepstake Annie.
What is the highest-rated movie like Sweepstake Annie?
Louis C.K.: Hilarious (2010), rated 7.8/10 by 321 TMDB users.
What is the newest movie like Sweepstake Annie?
Spa Weekend (2026) is the most recent release on this list.
Are there English movies like Sweepstake Annie?
Yes: Taking Care of Business (1990), 29th Street (1991) and Easy Money (1983).
How are movies similar to Sweepstake Annie chosen?
First come films that Trakt’s viewers watch alongside Sweepstake Annie, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.