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Movies Like The Sadder but Wiser Boy
Find movies like The Sadder but Wiser Boy using TMDB similarity plus Movie Rankings community context. Our top current pick is John Mulaney: The Comeback Kid. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.
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John Mulaney: The Comeback Kid
2015
Armed with boyish charm and a sharp wit, the former "SNL" writer offers sly takes on marriage, his beef with babies and the time he met Bill Clinton.
Chris 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
Jim Jefferies: Freedumb
2016
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
Bill 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.
Ricky 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.
Jim Jefferies: Intolerant
2020
Between scenes from an excruciating date, Jim Jefferies digs into generational differences, his own bad habits and the shifting boundaries in comedy.
Ricky Gervais Live 3: Fame
2007
The third of Ricky Gervais' themed live stand-up shows.
Jim Jefferies: This Is Me Now
2018
The gleefully irreverent Jefferies skewers “grabby” celebrities, political hypocrisy and his own ill-advised career moves in a brash stand-up special.
LaRoy, 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.
The Roast of Tom Brady
2024
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
Donald Glover: Weirdo
2012
Fearlessly funny stand-up comic and sitcom star Donald Glover puts on a live show in New York, confessing his love for Cocoa Puffs and Toys "R" Us.
Fun with Dick and Jane
1977
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Anuvahood
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.
How to Murder Your Wife
1965
Stanley Ford leads an idyllic bachelor life. He is a nationally syndicated cartoonist whose Bash Brannigan series provides him with a luxury townhouse and a full-time valet, Charles. When he wakes up the morning after the night before - he had attended a friend's stag party - he finds that he is married to the very beautiful woman who popped out of the cake - and who doesn't speak a word of English. Despite his initial protestations, he comes to like married life and even changes his cartoon character from a super spy to a somewhat harried husband.
After 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.
Chris D'Elia: Man on Fire
2017
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
Russell Peters: Almost Famous
2016
The comic comes home to Toronto to sound off on cultural quirks, furniture building and bathroom visits, revelling in all things ridiculously human.
Duplex
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!
What are the best movies like The Sadder but Wiser Boy?
John Mulaney: The Comeback Kid is the strongest current recommendation on this page for viewers looking for movies like The Sadder but Wiser Boy.
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