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Unlike other major streaming services, Prime Video features an extensive lineup of movies released before the year 2000, going all the way back to the earliest days of cinema. There are so many older movies available on Prime Video that it can be a bit challenging to find the right one to watch while scrolling through endless lists of random obscurities.
Still, there are plenty of older movies worth checking out on Prime Video, including some all-time comedy classics. Whether you’re up for a rom-com or an offbeat sketch comedy, Prime Video has you covered.
If you’re looking for a good laugh from a great movie, featuring some of the most talented performers and filmmakers in comedy history, here are my picks for three of the best classic comedies currently streaming on Prime Video.
‘Monty Python and the Holy Grail’
British comedy troupe Monty Python reached new creative heights with this freewheeling parody of medieval epics, featuring King Arthur and his Knights of the Round Table on an absurd quest for the Holy Grail. Monty Python members John Cleese, Eric Idle, Michael Palin, Graham Chapman, Terry Jones and Terry Gilliam all play multiple roles, with Gilliam and Jones serving as directors.
So many of the movie’s hilarious lines and set pieces have been indelibly enshrined in pop culture that people may be quoting them without even realizing it, but the source material remains fresh and funny even after decades of references and remixes. Monty Python’s surreal sense of humor mixes the sophisticated and the scatological, with fart jokes one moment and comedic deconstructions of classical literature the next — all equally entertaining.
Watch on Prime Video
‘UHF’
“Weird Al” Yankovic has become such a beloved figure in recent years that the box-office failure of his only theatrical feature film is a bit surprising. “UHF” is now a cult classic, though, with the same good-natured humor as Yankovic’s hit song parodies. “UHF” adds in movie and TV parodies as well, springing from the mind of oddball slacker George Newman (Yankovic), who finds himself managing a scrappy, small-scale TV station.
“UHF” is a love letter to the kind of low-fi local TV programming that no longer exists, and a perfect showcase for Yankovic’s unabashed goofiness. The supporting cast includes early roles for future sitcom stars Michael Richards of “Seinfeld” and Fran Drescher of “The Nanny,” eagerly embracing the movie’s exuberant, "let's put on a show" spirit.
Watch on Prime Video
‘Annie Hall’
One of the few comedies to win the Oscar for Best Picture, Woody Allen’s 1977 film set the template for decades of rom-coms to follow, with its charming and messy romance between Diane Keaton’s title character and neurotic comedian Alvy Singer (Allen). Allen combines the playful meta-commentary of his early films with the more grounded storytelling that characterizes his later work, bringing emotional depth to the central relationship along with memorable jokes.
Keaton deservedly won an Oscar for her performance as the vibrant Annie, who challenges Alvy’s assumptions about women and never lets him take the easy way out with her. The movie offers satire about entertainers and intellectuals, while treating its characters with sensitivity and grace, despite (or perhaps because of) their ridiculousness.
Watch on Prime Video
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