“It's All in My Head.”
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“It’s All in My Head.” The Top 300 Comedy Films of All-Time (in my opinion) my (in Esma relda Villa Lobos An Introduction Although the following is what I hope to be a comprehensive study guide on, in my opinion, the greatest comedy films of all time, if you happen to disagree with any of my critiques or choices throughout the course of reading this novel, please rest assured that this is by no means the last of these collections that I will assemble throughout my life and career. What started out as a list of ten became a list of twenty, twenty became fifty, fifty became one fifty, two hundred, two fifty and then finally three hundred. The pages are organized in descending order because what is the fun in giving away the best part fresh out the gate? I must admit that my final choices are altogether unsurprising, but frankly there is just no argument when it comes to the best of the best. I am certain your jaw will drop to the ground when you see some of the films that I have omitted (hint: you won’t find “Princess Bride” anywhere on this list) and I am also certain others will have you scratching your head and wondering “what?!” There are plenty of films on here that were bashed by “day-to-day” critics upon the time of their release, but since I am a “bigger picture” type of analyst, I find that these films, over time, show their worth and merit. If at any point in time you find yourself wondering, “how can I watch some of these films?” Well, if they aren’t available on Netflix, nine times out of ten you can rent them on Vudu for $2.99-$3.99 apiece. I believe in paying for films long after their opening box office weekend and I appreciate the business model of Vudu in such that I am giving money directly to a title instead of regularly paying membership to a platform filled with things I don’t watch. I don’t hate Netflix, but frankly, I want to give my money to Noah Baumbach without feeling like my dollars are going to a lot of the other drivel that comes out of that juggernaut of a subscription service. Either way, if you find the following controversial… cool. I’ll take controversy over boredom any day of the week. I sincerely hope that you enjoy. Xo, Esmarelda For mom & dad. 300. 300. Josie and the Pussycats (2001) Truthfully speaking, as far as my favorite movies go, this film should be much higher up on the list. The soundtrack is fantastic and stellar performances from Parker Posey and Allan Cumming sets this hokey teenage flick apart from the rest. Add to that the fact that this film gave us the fake boy band “DuJour” (Breckin Meyer, Seth Green, Donald Faison, and Alex Martin,) it all sets the stage for the perfect film to kickstart this list because personally I can’t resist the opportunity to showcase a fun pop punk fantasy centering around a plot to brainwash consumers through the power of technology. Check it out. Memorable Quote – “I want a Big Mac.” Rating – 3.5/5 Unicorns 299. 299. But I’m a Cheerleader (1999) Long before LGBTQ+ was a category on Netflix, there was Jamie Babbit’s colorful and hilarious tale of a straight cheerleader (Natasha Lyonne) who is sent to a rehabilitation camp when her family and friends all suspect that she is a lesbian due to her admiration of Georgia O’Keefe paintings. To date, this is my favorite on-screen RuPaul role (the second is also somewhere on this list), and the whole film is not only funny but an artistic marvel with undertones of a John Waters film. The cotton candy set design and vibrant colors add to an already fun and intriguing story that is supported by a dynamite cast of young and upcoming actors like Michelle Williams, Melanie Lynskey, and Clea DuVall. Cathy Moriarty as the evil camp director is a performance not to be missed. Memorable Quote – “But I’m a Cheerleader!” Rating – 3/5 Unicorns 298. 298. Men in Black (1997) “Men in Black” was the second highest grossing film released in 1997, and although it was considered somewhat of a technical marvel at the time for its creative visual effect's techniques, the real star here is the relationship between Will Smith and Tommy Lee Jones. Fun supporting characters like Tony Shaloub’s “Jeebs” and Rip Torn’s “Zed” add to the well-constructed and easy to follow plot sprinkled with memorable lines makes this one comedic sci-fi blockbuster that stands the test of time. If all of that weren’t enough, this film can be added to the “Linda Fiorentino Saves the World” narrative that was perpetuated throughout the late nineties in such a way that makes you think… whatever happened to her? Memorable Quote – “You know what the difference between you and me is? I make this look good.” Rating – 3/5 Unicorns 297. 297. Duplex (2003) Danny DeVito has only ever directed seven feature films, and four of them appear on this list. Just like “Death to Smoochy,” “Duplex” was a film that was universally panned by both critics and audiences upon it’s release. But having said that, I like “Duplex.” To me, it is a funny modern fairy-tale of a recently married couple who are trying to live out their happily-ever-after but are unable to due to the annoying hijinks of their aging upstairs neighbor. Drew Barrymore is sweet, Ben Stiller is funny, they are a good match together (makes you wonder why nobody ever paired them up again… they have good chemistry) and the movie as a whole is a highly enjoyable way to pass a few hours. Not only that, but if you throw Harvey Fierstein and Maya Rudolph in the mix, there’s really nothing to complain about so I’m not too sure why so many turned their noses up at this one. If you haven’t seen it, I highly recommend you give it a watch. Memorable Quote – “Bang. Bang. Bangity Bang. Baaaaaang.” Rating – 3/5 Unicorns 296. 296. The Freshman (1990) I’m going to keep this brief. Marlon Brando does a parody of Don Corleone and Matthew Broderick must figure out how to transport a Komodo dragon. It’s written and directed by Andrew Bergman, who in my opinion is one of the most under-talked about comedic screenwriters of the mid-seventies through late nineties. He doesn’t have a ton of projects under his belt, but the ones that he does have are a total gem. Bruno Kirby is Bruno Kirby and that’s always good enough for me. Check out the big brains on Frank Whaley while you’re at it. Memorable Quote – “I’m gonna puke my guts out.” Rating – 2.5/5 Unicorns 295. 295. Election (1999) Reese Witherspoon’s Tracey Flick is perhaps one of the most subtle but terrifying femme fatales of the last millennium in this funny and twisted tale of school politics. Also starring Matthew Broderick (now as a teacher instead of a recent college grad), Alexander Payne’s ode to class elections and the bubbling of a mid-life crisis is both intriguing and entertaining with Chris Klein doing what Chris Klein does best – playing a dumb jock. Memorable Quote – “Looks like you could use a cupcake.” Rating – 3.5/5 Unicorns 294. 294. Chasing Amy (1997) I have this theory that Ben Affleck thinks he is so good at pleasing a woman that he can turn any gay woman straight. This is not only reinforced by things he says in the charming “Chasing Amy” but also reiterated later on in the not-as-bad- as-everyone-says “Gigli” in 2003. So, can someone find one of Ben Affleck’s ex-girlfriends and ask how good he is in the sack, because according to two separate movies he is supposedly dynamite. Bonus note – girls don’t normally do it for me, but Joey Lauren Adams most certainly does. Memorable Quote – “You’re dating a guy?!” Rating – 3/5 Unicorns 293. 293. Go (1999) I love a good ensemble cast. I’ll just rattle off a few names: Jay Mohr, Taye Diggs, Katie Holmes, Sarah Polley, Scott Wolf, Timothy Olyphant, Breckin Meyer and William Fichtner all make up the elements of a fun story of a drug deal gone bad told from the point of view of three different parties. Oh, and a then-unknown Melissa McCarthy has a small part in it as well. File this one under “turn of the millennium teenage drug tales” that are quirky but fun to digest on a Sunday afternoon around 2pm. Directed by Doug Liman, one of my favorite non-auteur directors, the manic pace and colorful situations our many characters find themselves in will have you watching and wondering “wow… the late nineties were a little messed up.” Memorable Quote – “Are you Monty Hall?” Rating – 2.5/5 Unicorns 292. 292. Made (2001) “Made” is the directorial debut of future “Mandalorian” creator Jon Favreau. Puff Daddy is in it and other than that all you really need to know are the words “Cardiff Giant.” Can somebody please bring me some pizza? Memorable Quote – “Cardiff Giant.” Rating – 3/5 Unicorns 291. 291. Swingers (1995) So, when I first put “Go” at number 293, I had no idea it was directed by Doug Liman, but this is usually how things works so I’m not very surprised that I put it so close to “Swingers.” “Swingers” is also directed by Doug Liman, but I always think that it is directed by Jon Favreau.