Monty Python - Watch Order: Release Order

Other Watch Orders:
1971 - 19835 Films7h 40m4.4 Average

Monty Python brought their absurdist comedy from television to the big screen with five theatrical releases. This legendary British troupe created a unique blend of intellectual humor, surreal sketches, and satirical storytelling that influenced comedy for generations.

This Release Order includes all five films, though it's important to note that two are sketch compilations (And Now for Something Completely Different and Live at the Hollywood Bowl) while three are narrative feature films. The progression shows the Pythons' evolution from repackaging TV material to creating original cinematic works of increasing ambition and scope.

1
And Now for Something Completely Different poster

And Now for Something Completely Different

19711h 28m4.2
Director: Ian MacNaughton
Cast: Graham Chapman, John Cleese, Terry Gilliam, Eric Idle, Terry Jones

A collection of Monty Python's Flying Circus skits from the first two seasons of their British TV series.

Comedy
2
Monty Python and the Holy Grail poster

Monty Python and the Holy Grail

19751h 31m4.7
Director: Terry Jones
Cast: Graham Chapman, John Cleese, Eric Idle, Terry Gilliam, Terry Jones

King Arthur, accompanied by his squire, recruits his Knights of the Round Table, including Sir Bedevere the Wise, Sir Lancelot the Brave, Sir Robin the Not-Quite-So-Brave-As-Sir-Lancelot and Sir Galahad the Pure. On the way, Arthur battles the Black Knight who, despite having had all his limbs chopped off, insists he can still fight. They reach Camelot, but Arthur decides not to enter, as "it is a silly place".

AdventureComedyFantasy
3
Life of Brian poster

Life of Brian

19791h 34m4.6
Director: Terry Jones
Cast: Graham Chapman, John Cleese, Terry Gilliam, Eric Idle, Terry Jones

Brian Cohen is an average young Jewish man, but through a series of ridiculous events, he gains a reputation as the Messiah. When he's not dodging his followers or being scolded by his shrill mother, the hapless Brian has to contend with the pompous Pontius Pilate and acronym-obsessed members of a separatist movement. Rife with Monty Python's signature absurdity, the tale finds Brian's life paralleling Biblical lore, albeit with many more laughs.

Comedy
4
Monty Python Live at the Hollywood Bowl poster

Monty Python Live at the Hollywood Bowl

19821h 20m4.4
Director: Terry Hughes
Cast: Terry Gilliam, John Cleese, Graham Chapman, Eric Idle, Terry Jones

Monty Python perform many of their greatest sketches at the Hollywood Bowl, including several from pre-Python days.

Comedy
5
Monty Python's The Meaning of Life poster

Monty Python's The Meaning of Life

19831h 47m4.3
Director: Terry Jones
Cast: Terry Gilliam, Graham Chapman, John Cleese, Eric Idle, Terry Jones

Life's questions are 'answered' in a series of outrageous vignettes, beginning with a staid London insurance company which transforms before our eyes into a pirate ship. Then there's the National Health doctors who try to claim a healthy liver from a still-living donor. The world's most voracious glutton brings the art of vomiting to new heights before his spectacular demise.

Comedy