1. Monty Python and the Holy Grail
My funniest movie ever made is the same as a lot of people's. I first saw it in high school when my dad got the movie on VHS for Christmas and wanted to share it with me and my brother. We proceeded to laugh hysterically for the next 91 minutes so hard that I missed half the jokes and (gleefully) watched the movie again immediately after and probably twice a day for the next few weeks. I even wrote a two page poem in English class in iambic pentameter titled "The Ballad of Python" which scored me a near perfect grade from the toughest teacher in school. There's no point rehashing any of the bits here, nearly the whole movie has entered into the pop culture consciousness. I'll just say that my favorite bit changes each time I watch the movie. Much like the next movie on the list...
2. This is Spinal Tap
Unlike Holy Grail, Spinal Tap didn't hit me right away. I liked it well enough, but it didn't make much of an impression. I saw it again not too long after and really connected to the real life and occasionally subtle ridiculousness of it. The interplay between the band members, the zucchini in the pants, Stonehenge, and the DVD commentary helped me appreciate it even more. The commentary is done by Harry Shearer, Michael McKean, and Christopher Guest in character as Spinal Tap, commentating as though they were watching the "real documentary" that was made of them. This kind of meta approach to it brought my love for it to the fore and it's stayed there ever since. Again, I can't pick a favorite part or bit because it changes each time, but "these amps go to 11" and "it's like, how much more black could this be? And the answer is none. None more black" have gotten me every time.
3. Coming to America
One of the first comedies I was obsessed with, Eddie Murphy's best overall movie is also his funniest. While many of us remember and revere his (and Arsenio Hall and Clint Smith's) work as the barbershop characters, which is amazing, the last time I watched it I was really taken in by Murphy's work as Akeem, the prince. The chemistry he shares with Arsenio's Semmi is what really drives the movie. Akeem's naivete, his stiffness, and his heart is what rounds the character out, but he's also very subtly funny. The movie also, of course, does highlight Murphy's ability to play different characters, whether it's Akeem, Randy Watson ("give it up for my band, Sexual Chocolate!"), or Clarence and Saul the old Jewish man in the barbershop, Murphy is as brilliant as any comedian has ever been at inhabiting the different people and getting us to laugh.
4. Annie Hall
Woody Allen's masterpiece, I recently wrote about it when I placed it as my all-time #41 movie. Though many prefer the "earlier, funnier movies" from Allen, I don't. Though there are definitely some gem bits in them, Allen's pre-Annie Hall work is obviously that of a gag writer. With Annie Hall, Allen for the first time created real characters and let the humor come from behavior as well as some crazy one liners and whatnot. It was his first mature comedy, and in my mind still his best.
5. The Big Lebowski
Though I could've easily also chosen the Coen Brothers' great Raising Arizona, I decided to go with Lebowski because I've probably watched it as much as the rest of the Coen's movies combined. Jeff Bridges, Steve Buscemi, and especially John Goodman keep me coming back to this bowling noir movie. Not quite a parody of the old detective noir genre, but more a twisted modern take on it, the movie works even if it doesn't make you laugh. But The Dude, Walter, and Donnie always have me cracking up, and then there's John Turturro's Jesus, Peter Stormare and the nihilists, Philip Seymour Hoffman's awkward Brandt, and of course Sam Elliot's The Stranger narrating the whole thing and occasionally losing his way.
6. Office Space
Although it loses its steam in the last third of the movie, Office Space is a pretty perfect comedy for a good hour of its runtime. Created by Beavis and Butthead's Mike Judge, and failing at the box office upon release, it quickly built up word of mouth and is now one of the most beloved and acclaimed comedies of recent times. The mundanity on display, alongside the ridiculous, has an almost Seinfeld-ian quality to it that help to make it both universal and completely absurd. Of course, in the best ways possible. Maybe even more than Lebowski, Office Space has entered so many new bits to the pop culture comedic landscape it's mind boggling.
7. Superbad
Other than the McLovin storyline, for most of the runtime I think this is the most accurate to life high school movie I've ever seen. The main characters are juvenile, awkward, sex constantly on the brain, girl obsessed but without any communication tools to effectively talk with said girls being obsessed about, and many more painfully accurate traits. Then the ridiculous McLovin storyline is there and might've sank a lesser movie, but instead it helps lift this movie up. The actors are all game and doing great work, you can feel the friendship bonds between Seth and Evan, and McLovin's adventure with the worst cops in the world is hysterical in all its insanity and its break from reality. And the girls (Emma Stone and Martha McIsaacs) are funny, charming, and beautiful in a down to earth way. Also, there's a ton of dick jokes, so the movie pretty much has something for everyone.
8. Blazing Saddles
Another one of those that runs out of steam in the end, there may not be a funnier movie for the first half or even 2/3rds than Blazing Saddles. Crazy slapstick, biting satire, pure idiocy, stereotyping galore, and the most n-words this side of Django Unchained, Blazing Saddles is the ultimate "let's throw everything at the wall and see what sticks" movie from the master of said form, Mel Brooks. This is also one of those great 70's movies that wouldn't even get its script read today, much less be greenlit and actually filmed and released to the public. Thankfully, studios in the New Hollywood era were slightly riskier and we are all the better for it.
9. South Park: Bigger, Longer and Uncut
One of the craziest major movies ever released, I remember being 16-years-old and sitting in the theater with my dad and brother watching this movie. None of us knew it was a musical, which was kind of a disappointment, but we all loved South Park already, having watched it from the very beginning. I've rarely laughed harder than I did in that theater. I can still remember feeling uncomfortable sitting next to my dad while Saddam Hussein continuously pulls out giant dildos to tempt his lover Satan, only to look over and see my dad laughing his head off and thinking "ahh, cool". In other movies, that would be the most outrageous scene. In this movie, that doesn't even make the top 20, even as hilarious as it is.
10. Bowfinger
The last time Eddie Murphy was truly great in comedy (I think he was extraordinary in his dramatic turn in Dreamgirls) was in his dual roles in the Steve Martin written masterpiece Bowfinger. Though his awkward and scene stealing turn as the dorky Jiff is definitely his best, I think it has overshadowed his amazing work as Kit Ramsey, the biggest (and craziest) star in Hollywood. Steve Martin is low key, and many of the supporting players like Heather Graham, Terrence Stamp, and Christine Baranski get the most truly outrageous lines and scenes, but it's Murphy that makes this movie work. Jiff and Kit are so different, and so hilarious in their own odd ways. Steve Martin the writer definitely did his best work here, as the movie has wild set pieces, big broad comedy, small scenes that crackle with humor, funny throw away lines, and subtle commentary on Hollywood that really stings. Frank Oz does a great job of not letting the movie drag too much, and it's just a great fun time at the movies.
The honorable mention list of films that almost made it is long. The shortlist for this list was over 40 movies. While some of these may be better movies, they didn't make me laugh quite as much as those listed above. Or a couple make me laugh a lot but aren't pure comedies, so somehow didn't feel right. But I still wanted to list them in with the big group. A top 10 of the just missed are:
Groundhog Day
Some Like it Hot
Pulp Fiction
In Bruges
Our Hospitality (or The General or Sherlock, Jr.)
Swingers
Defending Your Life
Austin Powers: International Man of Mystery
High Fidelity
The Blues Brothers
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