So I want to give at least one of their movies a shot. Seen bits and pieces. What's considered their best and best place to start?

Holy Grail

The three movies are very different.

"The Meaning of Life" is closest to their Flying Circus tv series in that it's a collection of skits that showcase their unique sense of humor.

"The Holy Grail" is a single sustained narrative that feels like one of their skits expanded into a full-length feature.

"The Life of Brian" is an attempt at a more serious film, though it still features the Classic Monty Python sensibilities.

Brian is probably their best film, though Grail and Meaning are more representative of the group. All three, in addition to Flying Circus, are all worth watching.

Start with "And Now For Something Completely Different."

While this is a good "sampler", it's a compilation of clips from the tv show. I'd skip it and watch the show instead.
The theatrical features, unrestricted by tv censorship, allowed them to go all out. Two are rated R.

If it was me, I'd watch the tv show then the movies. Skipping And Now For Something Completely Different. It's all gold.

Holy Grail is the most accessible. If it doesn't make you laugh, their humor is probably not going to work for you.

Holy Grail is what made me realize that Monty Python just isn't for me. Actually, for the most part, British humor just doesn't work for me.

Most people consider Grail the best. Personally, I like Life of Brian better. I also like Grail, though honestly I'm not a big fan of Meaning of Life. I do love the series though.

If you want to start from something more traditional, and if you like that, go further and further off the rails and see if it works for you, I would start with Brian, then Grail, and Meaning of Life next.

If after that, you still dig it, definitely check out Flying Circus.

I think that Monty Python and The Holy Grail is their most accessible film but I tend to not like Monty Python that much either. I went through a span of time where I tried getting into them and have seen all their films plus a handful of episodes of the series and overall it doesn't do much for me. I tend to find British humor really works or just falls flat for me.

Personally love it all, but understand how many won't. Holy Grail is tied as my favorite movie of all-time, but perhaps watching a show or two (or the compilation film) would be a good appetizer to get a taste.

And while the series is spectacularly hilarious, I think Fawlty Towers is better, and more accessible from a typical American perspective.

Holy Grail and the TV show are the way to go.

Flying Circus has many moments of brilliant, wildly adventurous comedy, but I also like Fawlty Towers better. The greatest sitcom of all time, IMO.

Farty Towels is awesome

I agree with the Fawlty Towers being brilliant but I wouldn't consider it a good place to start for "Monty Python" films.

I'd start the *movies* with Monty Python and the Holy Grail as much as anything due to it feeling like a extended sketch from the show. After that go with Life of Brian, my personal favorite of the Python films, and then The Meaning of Life.

I'd start with a few pints. Perhaps something English. A nice dark ale.

It's not a compilation of clips from the show. It's more of a "best of." They re-shot their favorite sketches for this film (intended as an introduction for an American audience). The timing on these new versions is absolutely perfect and I actually prefer them to the original sketches. It's the perfect precursor to Holy Grail.

I would say between Holy Grail and Life of Brian. Based on your viewing habits, I think you may enjoy Brian more but Holy Grail is pure comedy quotable gold.

Going against the other answers, but first one I saw was Meaning of Life and I'd recommend that.

Holy Grail is one of my favorite comedies, but I rewatched it recently with some Python newbies and I could see it wasn't really connecting. I think Life of Brian has a clearer narrative and might be a better jumping-in spot.

The OP never established if he was a fan of the tv show. Not everybody gets them (or British humor). Since he never mentioned it, and was only asking about the movies, I assumed he was already familiar with them.

Have any of you rewatched Fawlty Towers in recent years? Try it. I did about 5 years ago and whereas once I thought it was very funny I now found it to be absolutely HORRIBLE. Nigh on unwatchable shit. It has not aged well in the slightest.

As for the Flying Circus, it was very hit and miss. ANFSCD was best to see them gather the best skits in one place. As for the movies Brian is easily the best. And I actually have a lot of love for the Meaning of Life. I would actually put the Holy Grail as the worst movie. And that is still pretty good.

Yes, I saw a few episodes of Fawlty Towers about two years ago and love it.

Wow. In all my years here, I've never read an opinion with which I disagree more. You win the forum today!