Best Prison Comedies to Watch

Description: Gene Wilder and Richard Pryor play two friends who are wrongfully convicted of robbery and sent to prison. Their attempts to survive and entertain their fellow inmates lead to a series of funny and memorable moments, culminating in a rodeo event.

Fact: The film was a major box office success, grossing over $100 million, making it one of the highest-grossing comedies of its time.

Description: While primarily a drama, this film has its share of comedic moments, especially through the character of Red, played by Morgan Freeman. The humor provides a counterbalance to the film's darker themes, making it a unique entry in this list.

Fact: Despite its initial lukewarm box office performance, it has since become one of the most beloved films of all time, often topping IMDb's Top 250 list.

Description: While primarily a drama, the film has moments of dark humor, especially in the interactions between the inmates and the warden, played by Robert Redford and James Gandolfini respectively.

Fact: The film was shot at the Tennessee State Prison, which was also used for filming "The Green Mile."

Description: This remake of the 1974 film stars Adam Sandler as a disgraced former NFL quarterback who ends up in prison and organizes a football game between the inmates and the guards. The humor comes from the underdog story, the camaraderie among the inmates, and the outrageous plays on the field.

Fact: The film features a mix of real-life athletes and actors, including NFL stars like Michael Irvin and Bill Romanowski. It also includes a cameo by Burt Reynolds, who played the lead in the original.

Description: While not set in a traditional prison, the film features a small-town Irish cop who, through his interactions with criminals and law enforcement, provides a comedic take on the idea of being "locked up" by one's own circumstances.

Fact: Brendan Gleeson's performance as the unconventional cop earned him a nomination for a Golden Globe for Best Actor in a Musical or Comedy.

Description: Will Ferrell plays a wealthy man who, after being wrongfully convicted, hires a car wash attendant (Kevin Hart) to prepare him for prison life. The humor comes from the cultural clash and the absurd preparation methods.

Fact: The film received criticism for its portrayal of race and stereotypes but was praised for the comedic chemistry between Ferrell and Hart.

Description: This early talkie features a mix of drama and comedy, showcasing life in a prison with a focus on the camaraderie and the absurdities of the prison system. The humor is more subtle, reflecting the era's comedic style.

Fact: It was one of the first films to win an Academy Award for Best Writing, highlighting its impact on early cinema.

Description: While not a comedy per se, the film's depiction of the meticulous planning and execution of the escape from the infamous prison has elements of dark humor, especially in the characters' interactions and the absurdity of their situation.

Fact: The film is based on the true story of Frank Morris and the Anglin brothers, whose escape from Alcatraz remains one of the most famous unsolved mysteries.

Description: Eddie Murphy and Martin Lawrence star as two friends who are wrongfully convicted of murder and sentenced to life in prison. Their journey through the decades, filled with comedic mishaps and the quest to prove their innocence, makes for a hilarious yet touching narrative.

Fact: The film spans from the 1930s to the 1990s, showcasing the evolution of prison life and societal changes over time.

Description: A man, seeking revenge for his father's wrongful imprisonment, gets himself sent to prison to torment the judge's son, only to find himself in a series of comedic misadventures. The film's humor lies in the absurdity of his plan and the prison environment.

Fact: The movie was directed by Bob Odenkirk, known for his comedic work on "Mr. Show."