Some Like It Hot (1959)
Marilyn Monroe was never taken seriously as an actress and comedienne, but just watching her keep up with comedy legends Jack Lemmon and Tony Curtis in Some Like It Hot is enough to see she was funnier than people gave her credit for. The film is really one of the most stacked comedies ever, with the aforementioned stars and director/screenwriter Billy Wilder and cinematographer Charles Lang (Sabrina, The Magnificent Seven, etc). It’s the perfect older comedy for people who swear that older movies aren’t funny. The smart dialogue isn’t delivered too quick for modern audiences. It’s silly enough to never get boring, but not outrageous enough that it’s campy. Some Like It Hot is a layered comedy that somehow springs more jokes the more you revisit it, but once you’ve seen it one time, you’ll gladly watch again. (Emily Kubincanek)
Dr. Strangelove, or How I Learned to Stop Worrying and Love the Bomb (1964)
While several of his films contain strokes of humor, Stanley Kubrick’s body of work isn’t exactly comedy-centric. Of course, when he decided to lean into that side of his personality as a filmmaker, he produced masterpieces like Dr. Strangelove. This rare foray into out-and-out comedy for the Stan is the best political satire of all time, and despite being rooted in Cold War anxiety, it’s still a topical farce to this day given current tensions pertaining to potential nuclear annihilation. The world is going to be obliterated someday, but as long as we have Dr. Strangelove we’ll still be able to laugh at our shared universal fears until the blast arrives. (Kieran Fisher)
A New Leaf (1971)
I laugh at funny comedies, but few make me lose my shit as powerfully as Elaine May‘s brilliant and dark directorial debut. She writes and co-stars too opposite a pitch-perfect Walter Matthau, in a story about a playboy who plans to marry a daffy millionaire and then murder her. Crazy dark, but also crazy funny as these two are absolutely priceless together. Make sure you’re not chewing or drinking anything during this one as you might just choke from laughter. And this isn’t news, but May is an unfortunate victim of Hollywood sexism. She directed a notorious bomb (Ishtar, 1987) and was then never given the opportunity to direct again, and it’s a loss for all of us. She had a triumphant partial return as the writer of The Birdcage (1996), but she deserved far more having previously gifted the world with films as diverse as The Heartbreak Kid (1972), Mikey and Nicky (1976), and Heaven Can Wait (1978). (Rob Hunter)
Blazing Saddles (1974)
What else can really be said about Blazing Saddles? The 1974 Mel Brooks film, about a black man becoming the sheriff of a racist, all-white town, is a classic lampoon of western films and a cornerstone of comedy. Despite its share of jokes and gags that could be considered not quite Kosher these days, it remains, for the most part, an equal parts hilarious parody of the outdated cowboy genre and a scathing critique of racial ignorance. It’s also incredible how well so much of the comedy holds up (and this is coming from someone who considers Tim & Eric’s Billion Dollar Movie a modern comedic masterpiece). It’s absurdist, slapstick, satire, and it still blazes forty-five years later.
Young Frankenstein (1974)
Co-written by Gene Wilder and Mel Brooks, this comedy is both an homage and parody of the 1930s Frankenstein films; it was filmed in black and white and used some of the original laboratory props. Wonderfully outdated sound effects including screeching violins and claps of thunder score the film to hilarious effect. Wilder, supported by a phenomenal cast including Marty Feldman, Cloris Leachman, Teri Garr, and, in a great cameo, Gene Hackman, plays the eponymous hero (villain?) as he unwillingly returns to the family castle to take up the mad scientist role in a new tale of Mary Shelley’s infamous monster. (Sam Olthof)
Monty Python and the Holy Grail (1975)
Whoever coined the idea that comedy is about subverting expectations probably did so after watching Monty Python and the Holy Grail. Like all of the best Python sketches, the film is pure silliness, and revels in doing the complete unexpected; from suddenly jump-cutting to a flashy intermission sequence that lasts for only a handful of seconds, to characterizing a seemingly harmless white rabbit as a flesh-eating monster. The film has also transcended any expectations of its original success to become one of the most iconic comedies of all time. It’s a rite of passage all its own, a legacy film to be passed down in a similar manner as Star Wars or Jaws or any other major outing of the 1970s; my own personal attachment to Holy Grail comes from my father showing it to me for the first time, maybe when I was too young, but it’s fine, because it’s been such a favorite for so many years. It also helps that the film is intensely quotable, so much so that referencing it has become a mark of a certain cultural fluency. Really, to say a cut is “just a flesh wound” or that someone’s father “smelled of elderberries” isn’t just silly; it makes sense at this point. (Christina Smith)
Breaking Away (1979)
Part look at working-class America, part underdog sports film, and all brilliant and funny, Peter Yates‘ late 70s masterpiece pits blue collar teens against privileged college kids, foreign professionals, and a severe lack of ambition. The result is magic. The four “townies” come to beautiful life through charismatic and memorable performance by Dennis Christopher, Dennis Quaid, Daniel Stern, and Jackie Earle Haley, each unique in character and persona, but absolutely unforgettable as a team. The characters are dealing with real strains, and much of the humor comes from those realities. Chief among them is the relationship between one of the boys and parents (played by the great Paul Dooley and Barbara Barrie) as his affections swoon through girls, the Italian racing team, and the beauty of doing your best. It’s a film that never fails to bring a smile and warm the heart, and that’s an increasingly rare feat these days. (Rob Hunter)
Monty Python’s Life of Brian (1979)
Holy Grail might be more quoted, but for my money, Life of Brian is better. And when you’re comparing Monty Python comedy, the bar is already very, very high indeed. In the whole Python repertoire, this film about an unwilling and wholly unqualified prophet is the least sketch-like, telling a cohesive story with a beginning, a middle, and a very definite end. And the story works beautifully, binding together unique characters, expertly delivered jokes and even aliens in a send-up of religion that’s as biting as you want it to be. Did I sing “Always Look on the Bright Side of Life” as my high school valedictory speech? I’ll never tell, but my mom has a VHS somewhere… (Liz Baessler)
9 to 5 (1980)
The workplace comedy is as American as it gets, and Colin Higgins‘ 1980 hit is not only a quintessential example of the sub-genre, but it’s also quite possibly the best. Everyone can identify with the daily frustrations of office politics, horrible bosses, and the general grind, but the film’s particular angle — women standing up for themselves in the workplace — was long overdue. Norma Rae (1979) may have arrived a year earlier, but Jane Fonda, Lily Tomlin, and Dolly Parton came guns blazing and armed with a steady stream of laughs. Dabney Coleman goes toe to toe with the ladies with equally entertaining results too. It’s a smart blend of wit, visual gags, and a serious agenda, and nearly forty years later it remains both hilarious and relevant. (Rob Hunter)
Related Topics: Comedy
