Monty Python and the Holy Grail. Hardcore Python fans will quote anything and everything at you, so you’re out of luck with them until you see it all. But Holy Grail is by far the most commonly referenced of the films by everyone else. You’ll also want to watch a number of sketches from Monty Python’s Flying Circus. You can get a lot of them on YouTube. Start with the Dead Parrot sketch and the Spanish Inquisition.
Life of Brian is indeed excellent, and one of my favorites. Sadly, it isn’t quoted as often as it should be. I think @seekingwolf gives a good ordering except that I’d definitely watch Life of Brian before Meaning of Life and I’d put the Election Night Special sketch in between Argument Clinic and Confuse a Cat.
I think you are right. Life of Brian, in my opinion, was still really funny but a bit more subdued than Meaning of Life. I think that should be watched first then to “prepare” you. If you aren’t offended by life of Brian (LOL) and have a great time, then watch Meaning of Life.
Get the boxed set of Flying Circus episodes. Some of the gags in the movies have roots in these. And they’re hilarious ! ...And relatively bite-sized servings of Python.
Among their movies I might like “Meaning of Life” most but each has special highpoints.
What type of humor do you like? The Cleese/Chapman written sketches tend to humor through confrontation, the Idle sketches humor through wordplay and the Palin/Jones sketches tend a bit more toward absurdist humor. Based on your answer I can tell you better what sketches to check out from Flying Circus (after you watch Holy Grail and Life of Brian though).
@asmonet I prefer to see you as pushing the OP towards a more fulfilling life my making him realize that, without Monty Python, his life till now has been about as fulfilling as that of a knight without any arms.
Holy Grail. It’s by far the most ubiquitous. I personally recommend them all, but even most non-Python fans have seen Holy Grail. It’s sorta one of those movies “everyone” has seen.
The Life of Brian really was Python’s finest hour. I loved The Meaning of Life too, although Cleese in particular hated the movie.
I’ve been known to perform this cheeky little number as a little sideshow at parties. Those little kids do love it so ;¬}
Definitely Holy Grail. Most people who continually reference Monty Python usually haven’t seen anything besides Holy Grail and Life of Brian. In terms of actual hilarity, see the show. It’s on Netflix now, I believe.