Movies Like Kippy Callahan: Puzzle Master of Days Gone By

If you liked Kippy Callahan: Puzzle Master of Days Gone By, a comedy movie directed by Rocco Comer-Romeo, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
2
Series 7 (2001)
★ 6.4/10Also comedy
A reality TV program selects six contestants to participate in a free-for-all, no holds barred deathmatch, where they must skillfully outwit and kill each other in order to be the last person alive.
3
Larry David: Curb Your Enthusiasm (1999)
★ 7.5/10Also comedy
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…
4
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
5
The Three Stooges (2012)
★ 5.8/10Also comedy
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
6
Cunk on Shakespeare (2016)
★ 7.4/10Also comedy
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…
7
The Wedding Year (2019)
★ 5.9/10Also comedy
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.
8
7 Days in Hell (2015)
★ 6.5/10Also comedy
A fictional documentary-style expose on the rivalry between two tennis stars who battled it out in a 1999 match that lasted seven days.
9
Amazon Women on the Moon (1987)
★ 5.9/10Also comedy
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…
10
Impractical Jokers: The Movie (2020)
★ 6.5/10Also comedy
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.
11
Sherlock Jr. (1924)
★ 8/10Also comedy
A film projectionist longs to be a detective, and puts his meager skills to work when he is framed by a rival for stealing his girlfriend's father's pocketwatch.
12
The Hangover Part III (2013)
★ 6.2/10Also comedy
This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.
13
The Adventure of Sherlock Holmes' Smarter Brother (1975)
★ 6/10Also comedy
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…
14
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
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.
15
Marvel One-Shot: All Hail the King (2014)
★ 6.8/10Also comedy
A documentary filmmaker interviews the now-famous Trevor Slattery from behind bars.
16
The Tramp (1915)
★ 6.5/10Also comedy
The Little Fellow finds the girl of his dreams and work on a family farm. He helps defend the farm against criminals, and all seems well, until he discovers the girl of his dreams already has someone in her life…
17
Tour de Pharmacy (2017)
★ 6.7/10Also comedy
A mockumentary that chronicles the prevalence of doping in the world of professional cycling.
18
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
19
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedy
Aziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
20
Die Hart (2023)
★ 5.9/10Also comedy
Kevin Hart - playing a version of himself - is on a death-defying quest to become an action star. And with a little help from John Travolta, Nathalie Emmanuel, and Josh Hartnett - he just might pull it off.