Movies like The Chicest Man in Roxie (1999)
The best movies like The Chicest Man in Roxie (1999) are I Love My Dad (2022), Pretty Persuasion (2005) and Jackass Presents: Bad Grandpa (2013). If The Chicest Man in Roxie hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedAnnie Hall (1977)7.7/10 from 4,400 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
I Love My Dad (2022)
A hopelessly estranged father catfishes his son in an attempt to reconnect.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisPretty Persuasion (2005)
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 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 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 · both comedy
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 · 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 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 thisAli Wong: Single Lady (2024)
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
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 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 thisA Bad Idea Gone Wrong (2017)
Two would-be thieves forge a surprising relationship with an unexpected housesitter when they accidentally trap themselves in a house they just broke into.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisTrailer Park Boys: Don't Legalize It (2014)
Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty deal. Meanwhile, Ricky’s dope growing business is under a major threat when the government announces a plan to legalize marijuana. Bubbles reluctantly joins them on his own quest to claim an inheritance left to him by his long-lost parents.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 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 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 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 thisWhy Worry? (1923)
A hypochondriac vacations in the tropics for the fresh air - and finds himself in the middle of a revolution instead.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAnnie Hall (1977)
New York comedian Alvy Singer falls in love with the ditsy Annie Hall.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisWayne's World (1992)
The adventures of two amiably aimless metal-head friends, Wayne and Garth. From Wayne's basement, the pair broadcast a talk-show called "Wayne's World" on local public access television. The show comes to the attention of a sleazy network executive who wants to produce a big-budget version of "Wayne's World"—and he also wants Wayne's girlfriend, a rock singer named Cassandra. Wayne and Garth have to battle the executive not only to save their show, but also Cassandra.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisMy Dream Is Yours (1949)
Conceited singer Garry Mitchell refuses to renew his radio contract, so agent Doug Blake decides to find a new personality to replace him. In New York, he finds Martha Gibson, a single mother with a great voice. He arranges for her to move to Hollywood, but then has a problem trying to sell her to the show's sponsor. Doug tries every trick he can think of to make Martha a star, and as the two work more closely, he falls in love with her. Complicating matters further, Martha meets and becomes attracted to Garry.
Why it matches: Similar story and style · both comedy
Station (1977)
The film focuses on the relationship between Gırgır Ali and a singer he has kidnapped. Gırgır Ali is a man who has been involved in many petty crimes throughout his life. Since his release from prison, he has been trying to live without committing crimes. One day, his old friend Palandöken asks Ali to kidnap the famous singer Yasemin. At first, Ali is reluctant to do so, but he decides to kidnap her himself to prevent others from doing so. The two spend some time together in an isolated mansion. Although Yasemin initially hates Ali, she will eventually be influenced by his lifestyle.
Why it matches: Similar story and style · both comedy
The American Mall (2008)
The executive producers of High School Musical keep the good times rolling with this upbeat musical comedy set in the one place every American teenager's home away from home - the local shopping mall. Ally (Nina Dobrev) is an optimistic adolescent singer/songwriter whose hard working mother owns the mall music shop frequented by every teen in town. When Ally shares her music with Joey (Rob Mayes), a janitor in the mall who harbors rock star ambitions, she is thrilled to find someone who can truly relate to her songs as well as her heart. Trouble looms on the horizon, however, in the form of the mall owner's spoiled rotten daughter Madison (Autumn Reeser). Madison is the kind of girl who's used to getting whatever she wants, and what she wants now could prove disastrous for both Ally's ambitions, and her mother's popular music store.
Why it matches: Similar story and style · both comedy
I Can Do Bad All By Myself (2009)
When Madea catches teenage Jennifer and her two younger brothers looting her home, she decides to take matters into her own hands and delivers the young delinquents to the only relative they have: their aunt April. A heavy-drinking nightclub singer who lives off of her married boyfriend, April wants nothing to do with the kids.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisPutney Swope (1969)
Swope—the only black man on the executive board of an advertising firm—is accidentally put in charge after the death of the chairman.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisBall of Fire (1941)
A group of academics have spent years shut up in a house working on the definitive encyclopedia. When one of them discovers that his entry on slang is hopelessly outdated, he ventures into the wide world to learn about the evolving language. Here he meets Sugarpuss O’Shea, a nightclub singer, who’s on top of all the slang—and, it just so happens, needs a place to stay.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisGreek Mothers Never Die (2025)
26-year-old Ella dreams of becoming a singer, but her overbearing Greek mother, Despina, insists she take over the gyros business and marry a Greek man. After her sudden death, Despina's larger-than-life presence refuses to fade, haunting Ella with even more unsolicited advice from beyond the grave.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like The Chicest Man in Roxie?
The closest matches to The Chicest Man in Roxie are I Love My Dad (2022), Pretty Persuasion (2005) and Jackass Presents: Bad Grandpa (2013). Below are 27 more, each with the reason it matches.
What should I watch after The Chicest Man in Roxie?
Start with I Love My Dad (2022), the closest match to The Chicest Man in Roxie.
What is the highest-rated movie like The Chicest Man in Roxie?
Annie Hall (1977), rated 7.7/10 by 4,400 TMDB users.
What is the newest movie like The Chicest Man in Roxie?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
How are movies similar to The Chicest Man in Roxie chosen?
First come films that Trakt’s viewers watch alongside The Chicest Man in Roxie, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.