Movies like Winning a Widow (1921)
The best movies like Winning a Widow (1921) are The Roast of Tom Brady (2024), Shane Gillis: Beautiful Dogs (2023) and The F**k-It List (2020). If Winning a Widow hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Winning a Widow
Quick picks
- Highest ratedRicky Gervais: Humanity (2018)7.6/10 from 547 votes
- NewestDriver's Ed (2026)Released 2026
The Roast of Tom Brady (2024)
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe F**k-It List (2020)
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMe Time (2022)
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
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 thisAmerican Dreamer (2022)
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisDriver's Ed (2026)
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAnuvahood (2011)
Kenneth (who likes to call himself Kay) begins to realise he's just another wannabe bad boy... even less than a loser in fact. After quitting his job at Laimsbury's, Kay vows to become a respected gangster... or cry trying. A pulls-no-punches, coming-of-age story, centering on one directionless hopeless "shotter", who finds his true worth in the face of urban adversity.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHeld Up (1999)
What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.
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 thisHannibal Buress: Comedy Camisado (2016)
He's a kamikaze gambler. A one-arm cuddler. And if his fly is down, so be it. A night of sly riffs and slow burns.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBill Burr: You People Are All The Same (2012)
Taking the stage in Washington, D.C., funnyman Bill Burr brings his stinging brand of humor to the spotlight, uncorking a profanity-laced, incisive routine that pokes fun at plastic surgery, reality TV, gold diggers and more.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 thisRicky Gervais: Humanity (2018)
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 thisDie, Mommie, Die! (2003)
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her husband. However, Angela's manipulative daughter, gay son and alcoholic maid are not going to make it easy for her.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAdam Sandler: Love You (2024)
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBill Burr: Drop Dead Years (2025)
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
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 Paper Tigers (2020)
Three middle aged men polish their martial arts skills to avenge their fallen master.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like this
Like Winning a Widow and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Winning a Widow?
The closest matches to Winning a Widow are The Roast of Tom Brady (2024), Shane Gillis: Beautiful Dogs (2023) and The F**k-It List (2020). Below are 17 more, each with the reason it matches.
What should I watch after Winning a Widow?
Start with The Roast of Tom Brady (2024), the closest match to Winning a Widow.
What is the highest-rated movie like Winning a Widow?
Ricky Gervais: Humanity (2018), rated 7.6/10 by 547 TMDB users.
What is the newest movie like Winning a Widow?
Driver's Ed (2026) is the most recent release on this list.
Are there English movies like Winning a Widow?
Yes: The Roast of Tom Brady (2024), Shane Gillis: Beautiful Dogs (2023) and The F**k-It List (2020).
How are movies similar to Winning a Widow chosen?
First come films that Trakt’s viewers watch alongside Winning a Widow, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.