Movies Like Carry On Jack

If you liked Carry On Jack (1964), a comedy and history movie directed by Gerald Thomas, 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
The Crimson Pirate (1952)
★ 7/10Also comedy
Burt Lancaster plays a pirate with a taste for intrigue and acrobatics who involves himself in the goings on of a revolution in the Caribbean in the late 1700s. A light hearted adventure involving prison breaks, an…
2
The Devil's Disciple (1959)
★ 6.6/10Also comedy and history
In a small New England town during the American War of Independence, Dick Dudgeon, a revolutionary American Puritan, is mistaken for local minister Rev. Anthony Anderson and arrested by the British. Dick discovers…
3
Captain Horatio Hornblower R.N. (1951)
★ 7/10Also history
Captain Horatio Hornblower leads his ship HMS Lydia on a perilous transatlantic voyage, during which his faithful crew battle both a Spanish warship and a ragged band of Central American rebels.
4
Tommy Boy (1995)
★ 6.8/10Also comedy
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
5
Taking Care of Business (1990)
★ 6.3/10Also comedy
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.
6
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
7
The Wonderful Story of Henry Sugar and Three More (2024)
★ 7.4/10Also comedy
Four tales unfold in Wes Anderson's anthology of short films adapted from Roald Dahl's beloved stories, "The Wonderful Story of Henry Sugar", "The Swan", "The Rat Catcher", and "Poison."
8
Swashbuckler (1976)
★ 6.2/10Also comedy
A pirate and a hot-tempered noblewoman join forces to protect Jamaica from a tyrant.
9
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
10
Private Valentine: Blonde & Dangerous (2008)
★ 6.2/10Also comedy
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain…
11
Hot Shots! (1991)
★ 6.6/10Also comedy
The gang that created Airplane! and The Naked Gun sets its sights on Top Gun in this spoof. Topper Harley is a talented but unstable fighter pilot with an axe to grind: clearing the family name. His mission is to…
12
Midway (2019)
★ 7.1/10Also history
The story of the Battle of Midway, and the leaders and soldiers who used their instincts, fortitude and bravery to overcome massive odds.
13
Wake Up, Ron Burgundy: The Lost Movie (2004)
★ 6/10Also comedy
While Ron Burgundy's rivalry with Veronica Corningstone escalates quickly, a group of unprofessional thieves better known as 'The Alarm Clock' try to make the truth known, whatever that may mean...
14
Hundreds of Beavers (2024)
★ 7.3/10Also comedy
In the 19th century, a drunken applejack salesman must go from zero to hero and become North America's greatest fur trapper by defeating hundreds of beavers.
15
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.
16
Once Upon a Deadpool (2018)
★ 7.1/10Also comedy
A kidnapped Fred Savage is forced to endure Deadpool's PG-13 rendition of Deadpool 2, as a Princess Bride-esque story full of magic, wonder, and zero Fs.
17
Oscar (1991)
★ 6.4/10Also comedy
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets…
18
Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)
★ 8.1/10Also comedy
After the insane General Jack D. Ripper initiates a nuclear strike on the Soviet Union, a war room full of politicians, generals and a Russian diplomat all frantically try to stop it.
19
Without a Clue (1988)
★ 6.8/10Also comedy
Sherlock Holmes is as dashing as ever, but with a little secret: Dr. Watson is the brains behind the operation. When Reginald Kincaid, the actor he has hired to play Holmes becomes insufferable, Watson fires him and…
20
The Bellboy (1960)
★ 6.2/10Also comedy
Stanley is a bellboy at the Fountainbleau Hotel in Miami Beach, where he performs his duties quietly and without a word to anyone. All he displays are facial expressions and a comedic slapstick style. And anything that…