Movies like The Sadder but Wiser Boy (2022)
The best movies like The Sadder but Wiser Boy (2022) are Held Up (1999), Anuvahood (2011) and After the Ball (2015). If The Sadder but Wiser Boy hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
The Sadder but Wiser Boy
Quick picks
- Highest ratedLouis C.K.: Hilarious (2010)7.8/10 from 321 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Held 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 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 thisAfter the Ball (2015)
After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who markets clothes "inspired" by the very designers Kate wants to work for. Who wants a spy among the sequins and stilettos? Reluctantly, Kate joins the family business where she must navigate around her duplicitous stepmother and two wicked stepsisters. But with the help of a prince of a guy in the shoe department her godmother's vintage clothes and a shocking switch of identities, Kate exposes the evil trio, saves her father's company -- and proves that everyone can wear a fabulous dress.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe 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 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 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 thisDuplex (2003)
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
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 thisLaRoy, Texas (2024)
Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.
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 thisDylan Moran: Like, Totally (2006)
Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like this2 Minutes of Fame (2020)
An up-and-coming stand-up comic moves to L.A. to pursue a film career after video clips of his act make him an online sensation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisRicky Gervais: Armageddon (2023)
Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisChris Rock: Kill the Messenger (2008)
An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDave Chappelle: Killin' Them Softly (2000)
Dave Chappelle returns for a stand-up to D.C. and riffs on politics, police, race relations, drugs, Sesame Street and more.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisRicky Gervais: Mortality (2025)
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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
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Frequently asked questions
What are the best movies like The Sadder but Wiser Boy?
The closest matches to The Sadder but Wiser Boy are Held Up (1999), Anuvahood (2011) and After the Ball (2015). Below are 17 more, each with the reason it matches.
What should I watch after The Sadder but Wiser Boy?
Start with Held Up (1999), the closest match to The Sadder but Wiser Boy.
What is the highest-rated movie like The Sadder but Wiser Boy?
Louis C.K.: Hilarious (2010), rated 7.8/10 by 321 TMDB users.
What is the newest movie like The Sadder but Wiser Boy?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like The Sadder but Wiser Boy?
Yes: Held Up (1999), Anuvahood (2011) and After the Ball (2015).
How are movies similar to The Sadder but Wiser Boy chosen?
First come films that Trakt’s viewers watch alongside The Sadder but Wiser Boy, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.