My Top Ten Favorite Comedy Movies
Posted on August 9, 2018
Well, we’re right in the middle of summer and at the theaters right now, people are lining up to see their favorite summer blockbuster action films. I love action films – and you can see my Top Ten Favorite Action Films right HERE – but I think one of my favorite genres is Comedy. Whenever my wife and I sit down to watch a movie during dinner, or whenever I want to wind down for the night if I’m by myself, I pop in one of my favorite comedy films. Just like the rest of the other Top Ten lists on my blog (you can see the entire list under the Categories tab on my main page, under Top Ten), this list is numbered for the purposes of this post, but in reality the films sort of fluctuate up and down on the list from time to time. Yet, overall, this list stays pretty much the same over time, consistently, which is how I know that they’re actually my top ten. Does that make sense? I hope so.
Let’s get to it!
10: HIGH FIDELITY (2000)
PLOT: Rob Gordon (John Cusack) is just an average Chicago record store owner (and compulsive list maker) who happens to be going through a break up with his girlfriend, Laura (Iben Hjejle). As his two employees, Dick (Todd Louiso) and Barry (Jack Black) attempt to cheer him up on their shifts at Championship Vinyl, Rob sifts through all of his past relationships to examine his all-time top breakups in order to make sense of his current situation and hopefully make things right.
WHY I LOVE IT: High Fidelity is really, truly, one of the all-time top underrated comedy films. The reason why it’s so low on my list is that, technically, it’s a romantic comedy. While I think rom-coms are fine, in general they don’t really have the same amount of laughs for me. However, I guess being a guy and having failed my own share of relationships made me identify with Cusack’s character, Rob, in a way that made all the laughs really hit home. On top of that, Jack Black gives one of his usual manic performances as Barry, and even Tim Robbins shows up as a foil to Rob as he tries to get into the pants of Laura. Honestly, if you have not seen this movie, please do yourself a favor and watch it. You won’t regret it, especially if you love Cusack. Also, I can’t help but note that Rob would love being on a list of top comedy films.
09: TEAM AMERICA: WORLD POLICE (2004)
PLOT: When the anti-terrorist organization known as Team America discovers that Kim Jong Il (Trey Parker) has a secret plan involving weapons of mass destruction, they enlist the help of actor and rising Broadway star Gary Johnston (Trey Parker) to infiltrate the terrorist’s ranks and discover what’s going on. With the help of the team’s financier, Spottswoode (Daran Norris) and his newfound teammates Chris (Matt Stone), Sarah (Masasa Moyo), Lisa (Kristen Miller), and Joe (Trey Parker) – Gary must use all of his training to save the world from Kim Jong Il’s dastardly plans.
WHY I LOVE IT: Though the entire film consists of puppets and props, the clever use of practical effects combined with an insanely funny script deliver this film up into the higher reaches of the comedy pantheon. Matt Stone and Trey Parker bring their South Park talents to this hilarious jab at American politics and military oversteps in the civilized world. All the music bits (I used to own the soundtrack on CD) and especially the hilarious vomiting scene are what keep this quirky film in my top ten. It rises slightly above High Fidelity almost solely because it’s not a rom-com, but lags behind others on this list because it’s almost more of an animated film than an actual feature film. Still, there’s not a time I’ve watched this that the jokes have become old.
08: NAPOLEON DYNAMITE (2004)
PLOT: In the small Idaho town of Preston, oddball teen Napoleon Dynamite (Jon Heder) tries to get through his day-to-day school life despite his even odder family and wacky schoolmates. When Napoleon befriends the new kid, Pedro (Efrem Ramirez), he finds himself helping Pedro run for class president. In the meantime, what to do about his meddlesome Uncle Rico (Jon Gries) and his internet-hogging brother Kip (Aaron Ruell)?
WHY I LOVE IT: We can all identify with Napoleon in some way and that’s certainly part of the draw for this 2004 film. What Napoleon Dynamite does really well, though, is produce comedy in lots of subtle and unexpected ways. What brings this film above the others for me is just that. It’s a comedy, but without being too over-the-top. The characters are really where the film shines, producing endless one-liners people still spout today – especially with Rico, Kip, and Napoleon himself. However, it falls behind some of the other films on my list because it’s a little too low-key, and many people miss its humor, meaning people generally either love or hate this movie. Still, it’s one of my favorites and I rewatch it at least once a year, in general.
07: AUSTIN POWERS: THE SPY WHO SHAGGED ME (1999)
PLOT: In a dastardly scheme to render Austin Powers (Mike Myers) powerless, Dr. Evil (Mike Myers) sends some of his agents to the 1960’s to request the aid of the portly Fat Bastard (Mike Myers) in stealing Austin Powers’ mojo. In order to get his mojo back, Powers must travel back in time to the swingin’ 60’s, and is helped in his quest by the sexy and fiery Felicity Shagwell (Heather Graham).
WHY I LOVE IT: Though it’s a sequel, The Spy Who Shagged Me is one of the rare cases in which the sequel is better than its predecessor. The jokes land more often and with better results, the characters are more interesting, and the cinematography and special effects are much sharper and flashy. Though I still like the other two films in the trilogy, this one will always be my absolute favorite. Mike Myers is at top-notch here, playing three different characters with the same comic energy and succeeding. Heather Graham is delightful, and even Will Ferrel shows up in a cameo as the hilarious Mustafa. This is all the hilarity and more of the original Austin Powers jammed into one slick package. Let’s hope that the rumors about a new Austin Powers movie are true!
06: NOT ANOTHER TEEN MOVIE (2001)
PLOT: “Plain” Janey Briggs (Chyler Leigh) is the object of ridicule at John Hughes High School, with her paint-covered overalls and her dorky glasses. When popular football star Jake Wyler (Chris Evans) seems to take an interest in her, she is suspicious. She should be, however, because little does she know that Jake has taken a bet to transform Janey into prom-queen material by the time prom rolls around.
WHY I LOVE IT: Not Another Teen Movie is a hilarious send up of several different films including the following: American Pie, American Beauty, Bring It On, Clueless, She’s All That, Road Trip, Can’t Hardly Wait, 10 Things I Hate About You, Never Been Kissed, and even the 1980’s classic The Breakfast Club. As far as a spoof film goes, it’s really top-notch, and the laughs don’t stop all the way through. There are lots of cameos from actors like Molly Ringwald and Paul Gleason (both from The Breakfast Club) and the main cast, including Chris Evans, Chyler Leigh, Jaime Pressly, Eric Christian Olsen, and Mia Kirshner all do a great job in their respective character archetypes. I would highly recommend this to anyone, especially if you’ve seen most of the movies it’s spoofing. Even without seeing the original films, the main story is stitched together well and provides a great sendup of teen movies in general, so really anyone can enjoy it.
05: THERE’S SOMETHING ABOUT MARY (1998)
PLOT: Ted Stroehmann (Ben Stiller) met the love of his life, Mary Jenson (Cameron Diaz) way back in high school. When he accidentally mucked things up, they both moved on. Now, living in Providence, Rhode Island as an adult man – Ted can’t stop thinking about Mary. When he hires a private detective named Pat Healy (Matt Dillon) to find her, Pat falls for her too, prompting Ted to take matters into his own hands.
WHY I LOVE IT: Ben Stiller is hands-down one of my favorite comedic actors of all time. In There’s Something About Mary, we get to see Stiller do some of his best work. This movie has some great charm, some very great jokes (the truck stop, anyone?), and even a musical number. While the story somewhat gets lost in the tangle of characters, the characters themselves more than make up for that. The Farrelly Brothers really struck gold with this film, and it’s definitely one you must own on Blu-Ray.
04: ANCHORMAN: THE LEGEND OF RON BURGUNDY (2004)
PLOT: In the wild world of newscasting in the 1970’s, there is one man who tells it like it is (at least as long as it’s on a teleprompter); San Diego’s Ron Burgundy (Will Ferrel). When an enterprising woman journalist named Veronica Corningstone (Christina Applegate) begins to rise to Burgundy’s level, Ron starts to worry about his job and so do the other guys from the news office. With a lot on the line, the news team must try to up their game if they want to stay relevant.
WHY I LOVE IT: Will Ferrell is really what holds this movie together. Though it’s chock-full of great scenes, great characters, and great actors – the story is sort of disjointed and inconsistent, which is why it’s not in my top three. However, the reason it’s above the others on this list is because it’s not an animated film, it’s not a spoof, and it’s not subtle. Anchorman is really just comedy at its best, and it can hold it’s own.
03: THE 40 YEAR-OLD VIRGIN (2005)
PLOT: Andy Stitzer (Steve Carell) is a nerd who is passionate about almost everything; Video Games, Karaoke, Painting Miniatures, Comic Books, and Action Figures. With all those hobbies, he’s just never had the time to have an actual girlfriend. When some work friends hear of Andy’s plight, they take turns trying to get him laid in a series of zany misadventures. However, through all the insanity, Andy sets his sights on a businesswoman next door named Trish (Catherine Keener).
WHY I LOVE IT: The 40 Year-Old Virgin is almost the perfect film. Steve Carell is perfect as everyone’s favorite virgin, Andy – and lots of comedic all-stars round out the rest of the cast, including Paul Rudd, Seth Rogen, and Jane Lynch. The film delivers lots of humor that could actually happen in everyday life, which puts it one notch above all the rest of the films listed before it. The reason it falls behind the other two entries is the slower pace. With scenes like the one in which Steve Carell is waxed (for real) – this movie deserves multiple re-watches over the years for me. If you can quote this film by heart, you are immediately someone I would like to be friends with.
02: ZOOLANDER (2001)
PLOT: When male model extraordinaire Derek Zoolander (Ben Stiller) is eclipsed by his rival, the enigmatic Hansel (Owen Wilson), he goes into modeling exile until a world-famous designer, Jacobim Mugatu (Will Ferrel), wants to work with him. After Zoolander is invited to a day spa, he is brainwashed by Mugatu’s right-hand woman, Katinka (Milla Jovovich), into trying to assassinate the Prime Minister of Malaysia. Only a plucky young reporter named Matilda Jeffries (Christine Taylor) stands in Mugatu’s way.
WHY I LOVE IT: Originally meant to be just a sketch for the 1996 VH1 Music Awards, Ben Stiller has gotten a lot of mileage out of his character Derek Zoolander. With a silly premise, Zoolander is one of those films that is intentionally “dumb” but which matches that knowing tone with lots and lots of jokes and gags that work. From the rivalry between Zoolander and Hansel, to the brilliant portrayal of Mugatu by Will Ferrel, there is so much going for this film, at least in my book. And the cameo by David Bowie is the icing on the cake. I guess the reason this isn’t in my number one spot is because it’s so “dumb”.
01: STEP BROTHERS (2008)
PLOT: Two thirty-something grown men, Brennan Huff (Will Ferrel) and Dale Doback (John C. Reilly), are forced to live together when their single parents fall for one another and end up moving in together. As the two “boys” mend fences with each other, they destroy everything around them with their immature hijinks.
WHY I LOVE IT: To me, Step Brothers is the perfect comedy film. It’s got the right amount of smart comedy and dumb comedy mixed together. There’s hardly a single moment in the film that feels off balance, and the casting is amazing. Both Reilly and Ferrel do a much better job in this film than they did in Talladega Nights, and you can tell the entire cast and crew must have had an absolute blast shooting the movie. There will be no other movie that is so quotable, at least in my opinion, for some time to come. From the “Boat” rap, to the epic front yard fight, Step Brothers is pure comedy gold. My wife and I love the movie so much, we each got it for each other on our first Christmas together. The movie is now “our” Christmas movie.
Well, there you have it. My Top Ten Favorite Comedy Films. If you have your own list, or any suggestions, please feel free to drop a line in the comments. As always, I will leave you with some honorable mentions.
- Talladega Nights
- The Jerk
- The Hangover
- The Big Lebowski
- Raising Arizona
- Billy Madison
- Tropic Thunder
- Wedding Crashers
- Starsky & Hutch
- Wet, Hot American Summer
- Walk Hard: The Dewey Cox Story
- Tucker and Dale VS Evil