Movies like Kippy Callahan: Puzzle Master of Days Gone By
The best movies like Kippy Callahan: Puzzle Master of Days Gone By are Cunk on Shakespeare (2016), Larry David: Curb Your Enthusiasm (1999) and How to Irritate People (1969). If Kippy Callahan: Puzzle Master of Days Gone By hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedJohn Mulaney: Kid Gorgeous at Radio City (2018)7.9/10 from 259 votes
- NewestChildish Things (2025)Released 2025
Cunk on Shakespeare (2016)
Fresh from her triumphs on Charlie Brooker's Weekly Wipe investigating time, Winston Churchill, and Donald Trump, Philomena Cunk has finally been given her own show - about William Shakespeare. Cunk will leave no stone unturned as she gets to the bottom of the Bard, visiting his birthplace, exploring the Globe, studying priceless artefacts and interviewing literally six different experts.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisLarry David: Curb Your Enthusiasm (1999)
Mock documentary about Seinfeld writer Larry David featuring contributions from his friends and colleagues. Larry makes a return to stand-up comedy and prepares to film a television special for HBO. This is the original special that gave birth to the long-running award-winning HBO series.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisHow to Irritate People (1969)
A pre-Monty Python mockumentary, written by and presented by John Cleese, that provides tips on learning how to irritate people.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Rutles: All You Need Is Cash (1978)
The story of the rise and fall of the Pre-Fab Four.
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 this7 Days in Hell (2015)
A fictional documentary-style expose on the rivalry between two tennis stars who battled it out in a 1999 match that lasted seven days.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDave Chappelle: The Closer (2021)
As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Adventure of Sherlock Holmes' Smarter Brother (1975)
After spending decades living in the shadow of his more famous and successful sibling, Consulting Detective Sigerson Holmes is called upon to help solve a crucial case that leads him on a hilarious trail of false identities, stolen documents, secret codes... and exposed backsides.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Mighty Wind (2003)
Three eclectic, never-quite-famous folk bands come together for the first time in decades following the death of their manager to put on an reunion concert in his honor, at the request of his son.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMe and My Pal (1933)
On the morning of his wedding to oil baron Peter Cucumber's daughter, Ollie receives a jigsaw puzzle from Stan as a wedding gift. The boys soon become absorbed in the puzzle. A taxi driver, butler, policeman and messenger boy join in as well.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTour de Pharmacy (2017)
A mockumentary that chronicles the prevalence of doping in the world of professional cycling.
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 thisFear of a Black Hat (1994)
Chronicling the controversial career of bad boys N.W.H. (Niggaz With Hats), this uproarious 'mockumentary' lampoons all of hardcore rap's hot-button issues. This underground laugh riot recounts the rise, fall and resurrection of a clueless bunch of would-be rappers, Ice Cold, Tone-Def & Tasty Taste performing as N.W.H.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohn Mulaney: Kid Gorgeous at Radio City (2018)
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisImpractical Jokers: The Movie (2020)
The story of a humiliating high school mishap from 1992 that sends the Impractical Jokers on the road competing in hidden-camera challenges for the chance to turn back the clock and redeem three of the four Jokers.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCunk on Life (2024)
Pioneering documentary maker Philomena Cunk returns with her most ambitious quest to date: venturing right up the universe and everything to examine life and existence in an attempt to find out the point of it all. Along the way, she interrogates experts on subjects from the big bang to biology and art to artificial intelligence. Really get to the nub of it.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisSarah Silverman: We Are Miracles (2013)
In her first-ever HBO solo special, Sarah Silverman takes the stage for an evening of adults-only stand-up comedy. Taped live in front of an intimate audience of 39 fans at Largo, a music and comedy club in Los Angeles, Sarah Silverman: We Are Miracles features Silverman taking aim at such subjects as cell-phone porn, crazy religions, specialty deodorants, terrible roommates, eyebrow waxing, her 19-year-old dog, Obama and Republicans, having babies, Pixar movies, the miracle of existence, and more.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Happiest Days of Your Life (1950)
Nutbourne College, an old established, all-boys, boarding school is told that another school is to be billeted with due to wartime restrictions. The shock is that it's an all-girls school that has been sent. The two head teachers are soon battling for the upper hand with each other and the Ministry. But a crisis (or two) forces them to work together.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAmazon Women on the Moon (1987)
Centered on a television station which features a 1950s-style sci-fi movie interspersed with a series of wild commercials, wacky shorts and weird specials, this lampoon of contemporary life and pop culture skewers some of the silliest spectacles ever created in the name of entertainment.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 thisCosmetic Criminals (2024)
A short mockumentary detailing the rise of intergenerational cosmetic theft through the eyes of an affected family.
Why it matches: Similar story and style · both comedy
Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)
Kazakh journalist Borat Sagdiyev travels to America to make a documentary. As he zigzags across the nation, Borat meets real people in real situations with hysterical consequences. His backwards behavior generates strong reactions around him exposing prejudices and hypocrisies in American culture.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisLittle Lunch: The Halloween Horror Story (2016)
When Mrs Gonsha's class puts on a Halloween play about a boy who leaves behind his friends for a scary new place, it hits too close to home for one student.
Why it matches: Similar story and style · both comedy
R65: The Silver Generation (2007)
This work is a mockumentary about the love for the silver generation.
Why it matches: Similar story and style · both comedy
Childish Things (2025)
A 30-year-old musician questions his resolve to marry his longtime girlfriend when he meets a free-spirited woman on his cross-country roadtrip.
Why it matches: Similar story and style · both comedy
Exquisite Corpse (2025)
Documentary about the eccentric figure of Mario Bazterrica Oliver. Following his recent death, various interviewees analyse, remember and portray, from multiple points of view, the importance and meaning of his person and his actions, which made him an important and not very popular person in Mallorca.
Why it matches: Similar story and style · both comedy
Bob Roberts (1992)
Millionaire conservative Bob Roberts launches an insurgent campaign against incumbent senator Brickley Paiste, firing up crowds at his rallies by singing '60s-style acoustic folk songs with lyrics espousing far-right conservative social and economic views.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Proper Care & Feeding of an American Messiah (2009)
'The Proper Care & Feeding of an American Messiah' is the mockumentary story of a man who thinks he is a messiah. Not *the* messiah, but rather a local, regionally selected messiah for his own home-town. He's on a quest, desperately trying to raise money for a town-wide rally where he hopes to announce his deity - and to determine his true, god-given 'special purpose' in life - which may or may not have something to do with ailments of the lower gastrointestinal tract, but he won't be sure until he hears more or less directly from Yahweh.
Why it matches: Similar story and style · both comedy
Drop Dead Gorgeous (1999)
In a small Minnesota town, the annual beauty pageant is being covered by a TV crew. Former winner Gladys Leeman wants to make sure her daughter follows in her footsteps; explosions, falling lights, and trailer fires prove that. As the Leemans are the richest family in town, the police are pretty relaxed about it all. Despite everything, main rival (but sweet) Amber Atkins won't give up without a fight.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Blair Bitch Project (1999)
Three student filmmakers run into trouble in the woods as they set out to make a documentary about the Blair Witch. This is a short parody of "The Blair Witch Project".
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Kippy Callahan: Puzzle Master of Days Gone By?
The closest matches to Kippy Callahan: Puzzle Master of Days Gone By are Cunk on Shakespeare (2016), Larry David: Curb Your Enthusiasm (1999) and How to Irritate People (1969). Below are 27 more, each with the reason it matches.
What should I watch after Kippy Callahan: Puzzle Master of Days Gone By?
Start with Cunk on Shakespeare (2016), the closest match to Kippy Callahan: Puzzle Master of Days Gone By.
What is the highest-rated movie like Kippy Callahan: Puzzle Master of Days Gone By?
John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.
What is the newest movie like Kippy Callahan: Puzzle Master of Days Gone By?
Childish Things (2025) is the most recent release on this list.
Are there English movies like Kippy Callahan: Puzzle Master of Days Gone By?
Yes: Cunk on Shakespeare (2016), Larry David: Curb Your Enthusiasm (1999) and How to Irritate People (1969).
How are movies similar to Kippy Callahan: Puzzle Master of Days Gone By chosen?
First come films that Trakt’s viewers watch alongside Kippy Callahan: Puzzle Master of Days Gone By, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.