Ten Classic Comedy Films You Must See Before You Die

You may just die laughing

Over the past month I have published two pieces that have elicited far more comments than any of my other 300-plus articles: “Ten Classic Westerns You Absolutely Must See Before You Die” and “Ten Classic War Movies You Must See Before You Die.” Reading the comments has been almost as much fun as it was writing the things, and because I’m a sucker for punishment, today I’m moving into that most subjective of film genres: the comedy.

Comedy has always been an entertainment battleground, and for good reason. While there are certain parameters required for something to be considered a good war, western, or even horror film, with comedy the boundaries are considerably fuzzier. Some people think the screwball comedy of the Marx Brothers was the height of the genre, others lean more toward the parody of Airplane! or The Naked Gun, and some will only accept the dry, cerebral humor found in Annie Hall or Manhattan.

What this means as far as this article is that many of you will scoff at my choices as ridiculously juvenile, while ranting that [insert film title here] was clearly the greatest comedy known to man. Maybe you’re right, and maybe you wouldn’t know funny if it hit you in the face with a pie. Either way and in no particular order, these are a few I think everyone should see. Give me some of your favorites in the comments.

O Brother Where Art Thou? (2000). The Coen Brother’s reimagining of Homer’s Odyssey in 1930s Mississippi is the one movie on this list where the soundtrack is as good as the film. It’s one I tend to quote in everyday conversation, though I do get odd looks when I say: “I’m a Dapper Dan man” or “I’m the paterfamilias!” And George Clooney should have won an Oscar for his facial expressions alone.

Office Space (1999). If you’ve never worked in a cubicle-farm office job you may not be able to fully appreciate the brilliance of this film, but anyone who’s worked any job has had a boss like Bill Lumbergh. We’ve also all heard some version of his dreaded line: “Um, yeah, I’m gonna need you to come in on Saturday.” For however brief a period, Peter Gibbons (played perfectly by Ron Livingston) gets to live the “it’s not that I’m lazy, it’s that I just don’t care” life we all dream of. Maybe the Great Resignation movement of 2021 is proving it’s not just a dream after all.

Stripes (1981). For me, Bill Murray’s best film ever and believe it or not, this movie is a more accurate depiction of Army life than 90% of the war movies out there. Besides being Murray’s first big hit after his time on Saturday Night Live, it was the first of his on-screen collaborations with Harold Ramis (Ramis wrote the screenplay for Murray’s 1979 film Meatballs) that would include Ghostbusters and Groundhog Day. It featured early performances by John Candy, John Larroquette, and Judge Reinhold as well as veteran actor Warren Oates perfectly cast as Sergeant Hulka. It’s also one of the most quotable films ever. It gave me lines I use to this day: “And then depression set in;” “I’m not parking it, I’m abandoning it;” “Ma’am, I’m sure there are a lot of ways I’ve gone that you haven’t,” and the ever useful “I don’t think I’ve ever been this happy” after getting a shoeshine.

Chasing Amy (1997). Picking this one runs the risk of offending both those who hate Kevin Smith and those who think he is the greatest filmmaker ever. Those who hate his work really hate it, and those who love it would be more prone to put Clerks here instead (I love Clerks as well, and also do not understand the vitriol cast at Mallrats by nearly everyone). Chasing Amy makes the list because it is Smith’s best and most mature film, features a completely over-the-top performance by Jason Lee, and should have made Joey Lauren Adams a star. Yet for all the praise she received for her role as Amy, this did not happen. Hollywood is dumb.

Ferris Bueller’s Day Off (1986). It would not be a stretch to include only John Hughes movies on this list (maybe I’ll do a separate one for him someday) since the man gave us everything from National Lampoon’s Vacation to The Breakfast Club to Home Alone; he’s the Steven Spielberg of the comedy genre. For me, though, this glorious chronicle of one teen’s determination to make the most of a day skipping school stands above all Hughes’ other films. Ferris (played by Matthew Broderick) does more with that one day off than most of us do in a lifetime and all with absolutely no consequences, no mean feat in itself. The film also started the trend of the now-expected end credit scene; at least Deadpool had the decency to copy it directly. Save Ferris.

Deadpool (2016). I was determined to include a Marvel film on this list because, well, Marvel. Though Thor: Ragnarok came close, even it can’t really be considered a comedy. However, now that Marvel owns Deadpool, I can skirt the issue this way. You would be hard-pressed to find more one-liners crammed into a single movie that has nonstop laughs amid the highest body count this side of a 1980s Schwarzenegger film. Ryan Reynolds went from “that guy who bombed in Green Lantern to the most famous Canadian not named Celine Dion in one outstanding performance.

High Fidelity (2000). I wasn’t sure about including this one at first, since it comes perilously close to falling into the dreaded Rom-Com subcategory. In the end, I simply could not leave off a film that would make my list of favorites in any genre. After all, it’s centered around music, a record store, Top 5 lists, and the earliest heartbreaks we suffered, with a Springsteen cameo and Jack Black run amok. Anyone who loves music has dreamed of owning a record store, sitting around with their friends debating which bands were the best, and getting paid to do it. Why wouldn’t you want to watch this one repeatedly?

Midnight Run (1988). This criminally underrated pairing of Robert DeNiro and Charles Grodin is one of the great buddy pictures of all time. We already knew the comic genius the late Charles Grodin possessed; the biggest surprise was seeing DeNiro’s ability as a comic actor, something not even hinted at in his previous dramatic performances. The premise of a bounty hunter dragging a bail-jumping, mob-connected criminal across the country doesn’t sound like the funniest premise on paper, but it absolutely is.

Animal House (1978). You always remember your first time, and this was the first “adult” comedy I ever saw, at 12 years old. Actually, my brother took me to see Blazing Saddles when I was 8, but I didn’t understand half the jokes then and was too busy tallying up the things I needed to mention in Confession the next day, so I count Animal House as my first. The sheer lunacy of the Delta House oddballs still cracks me up to this day (men stop developing emotionally and psychologically at 12 anyway, so no surprise there). It’s a perfect ensemble piece, and any scene with John Belushi is funnier than 90% of the comedy put out today. Seeing it now just reminds me how great a loss it was losing him at such a young age.

Groundhog Day (1993). Did Bill Murray just get a second movie on this list? Yes he did, and I came close to adding a third (Meatballs); I resisted only because I have already sung the man’s praises in an earlier article. Groundhog Day is considered by many the greatest comedy of all time, and it’s hard to argue with them. Watching Murray navigate the same day over and over again with hilarious results never gets old (film geeks more mathematically inclined than me calculate that he actually relived the same day for 12,395 days, or roughly 34 years). This film is so iconic that it created a new definition for the phrase “Groundhog Day.” Webster’s dictionary now has two entries for the phrase:

Groundhog Day (noun)

1: February 2, observed traditionally as a day that indicates six more weeks of winter if sunny or an early spring if cloudy

2: a situation in which the same, usually negative or monotonous experiences occur repeatedly or are felt to occur repeatedly with no change or correction

Unlike my earlier movie lists, I am sticking firmly to ten with this one. However, I must include the following honorable mentions, if only to reduce the number of snarky comments. Just missing the cut were Meatballs, Young Frankenstein, Clerks, Monty Python and the Holy Grail, Beverly Hills Cop, Caddyshack, and The Big Lebowski. Let me know your favorites, and as I am well aware that I’m an idiot, there’s no need to overemphasize it in the comments. Happy viewing.

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