15 Greatest Comedy Movies Produced by the Boomer Generation

The baby boomer generation was the result of GIs returning from World War II and going to college, purchasing homes, and starting families. Many were drafted to fight in Vietnam, and those that weren’t, watched the first televised war tear their friends to pieces. It’s a unique generational sentiment, watching one’s government transform from the heroes of the 1940s to the manipulative phonies of the 1970s. The cinema they produced was very much a response to that shift.

Once Vietnam was over, the whole country needed a good laugh. It just so happened that oddball writers, producers, and actors were coming out of the woodwork, feeding us talent from Chicago (Bill Murray, Harold Ramis, John Belushi), Canada (Dan Aykroyd, Lorne Michaels), and Harvard (Doug Kenney, Harry Shearer).

The comedies of the period are marked by their vast differences to one another; the studio system was at its most liberal, allowing writers and directors to experiment. It was risky, but the results were some of the most internationally recognizable, complex, and hilarious films of all time. These are the greatest comedy films created by members of the boomer generation.

15 The Sting (1973)

The second collaboration between stars Paul Newman, Robert Redford, and director George Roy Hill, after 1969’s wildly successful Butch Cassidy and the Sundance Kid, was another period piece crime caper, The Sting.

It’s smart plot, the classic con artist film. Newman’s the old hand, Redford’s the scrappy neophyte, and renowned character actor Robert Shaw is the mark. There’s pinstripe suits, street cons, betrayals, double- and triple-crosses, and a lot of cracking wise in between. The story weaves around lampposts and burrows beneath fences to tell a complex story, never letting the audience know too much at once, dazzling them with charm and one-upsmanship from the coolest pair of actors this side of an Ocean’s film.

Stream it on The Criterion Channel

14 Diner (1982)

The first feature film from director Barry Levinson, Diner carried a lot of autobiographical themes for the Baltimore native.

It’s a quarter-life coming of age tale about a group of friends as they navigate dates, marriage, pregnancy, and unnatural levels of sports fandom. Their 50’s-era tweed sports coats and skinny ties bely the silliness of their frivolous bickering, while all around them swirls the looming shadow and responsibility of adulthood. Some manage better than others, able to hold it together amid relationship troubles and bad habits left over from youth. The humor comes from the realism of the dialogue and characters, and the friction caused by their individual neuroses.

Helping launch the careers of Paul Reiser, Mickey Rourke, Ellen Barkin, and Kevin Bacon, it’s rarely laugh out loud, but the personality clashes and out-there peccadilloes make the viewer nostalgic for a place and time they may never have even lived through.

Stream it on Max

13 M*A*S*H (1970)

It’s the original film that famously spawned a TV show that lasted about three times longer than the war it’s based on. Robert Altman’s M*A*S*H*, a military acronym which stands for Mobile Army Surgical Hospital, follows the lives of military doctors and nurses throughout the Korean War in the early 1950s.

Related: Best Robert Altman Movies, Ranked

Despite their steely medical savvy, the main surgeons, Hawkeye, Duke, and Trapper John, spend their free time carousing, drinking, pulling pranks, and trying to get under the skin of Bible-thumping hard case Frank, and his nurse protege-turned-secret affair Hot Lips Houlihan, so named for their bawdy talk the surgeons slyly broadcast to the camp.

It’s a dark comedy, and the antics are presented as the kind of necessary respite from the horrors of field surgery in wartime. The burden carried by the characters, while simultaneously still managing to crack wise, is what makes this such a classic.

Rent it on Apple TV

12 Caddyshack (1980)

Caddyshack was the second comedy classic from the creator of National Lampoon, emotionally troubled wunderkind Doug Kenney. Combining recently famous SNL powerhouses Chevy Chase and Bill Murray with standup legend Rodney Dangerfield, as well as first-time director Harold Ramis, turned out to be the secret ingredients for another subversive look at class politics.

The golfers are rich, egomaniacal, and prissy. The caddies and country club workers are all young and cool. The groundskeeper is nuts. That’s the premise to Caddyshack, and despite putting every check-pattern-pansted doofus who ever swung a club in its crosshairs, it became a classic among the very people it lampooned. Vietnam was over, Reagan was just coming into office, and the yuppies were about to take over. In a preemptive F-you, this film reminded us to eschew exclusivity. So we’ve got that going for us, which is nice.

Rent it on Amazon Prime Video

11 Kelly’s Heroes (1970)

There’s not a lot of WWII comedies. Kelly’s Heroes makes it work. Sure, it stars Clint Eastwood, who finds it difficult to score laughs without an orangutan to lean on (like he did in Every Which Way But Loose), but the supporting cast pick up the slack. Don Rickles leads the charge of comedic character actors, not least of which is Donald Sutherland, as scene-stealing tank commander Oddball.

“Always with the negative waves, Moriarty.”

They’re seeking a cache of Nazi gold behind enemy lines, and the ridiculous characters only feed the even more ridiculous bureaucratic maneuvers, satirizing the very military that allows its members to commit a heist while wearing its uniforms. It’s an endlessly quotable flick, and even the massacre scenes are played for laughs.

Rent it on Apple TV

10 Back to School (1986)

Back to School was a vehicle for Rodney Dangerfield, plain and simple. Rodney’s a successful business owner who tries to convince his son to stay in school by re-enrolling in college to earn the Bachelor’s degree he never got.

Rodney had already successfully pivoted his standup persona to workable, if sometimes unbelievable, movie characters in Caddyshack and Easy Money. As the oldest and richest freshman at school, he remodels the dorms to match his quality of life, bribes author Kurt Vonnegut to write his term paper, parties all the time, all while managing to fall in love with his literature professor.

“What do you think? Someone else wrote this?”

“Look, all I know is that you didn’t, and that’s what disappoints me. I’ll tell you something else, whoever did write it doesn’t know the first thing about Kurt Vonnegut.”

He learns the error of his ways, rekindles his relationship with his son, and manages to win the school diving meet with his patented Triple Lindy. It’s far-fetched, formulaic, and damn funny.

Stream it on Amazon Prime Video

9 Harold and Maude (1971)

Harold and Maude is the sort of black comedy that was so much a product of its time, and a model for all future quirky rom-coms. It’s not that you couldn’t make it today; it’s more like, who would?

Harold is a wayward young man, privileged but out of place, constantly staging fake suicide scenarios to freak out the squares in his life, particularly his detached and cold mother, who wants her son to live a normal life. When she gifts him a Jaguar, he converts it into a hearse. When he meets septuagenarian Maude, whom he finds out was a survivor of Nazi concentration camps, he comes to thrive on her lust for life, and hilarious habit of petty theft. They begin a romantic relationship, grossing out everybody in Harold’s life, blind to the rich connection shared between the unlikely soulmates.

“A lot of people enjoy being dead. But they’re not dead, really. They’re just backing away from life.”

It’s a tragicomic ending, playing with the viewer’s expectations, and yet so full of catharsis, like having a good cry after a funeral.

Stream it on Paramount+

8 Trading Places (1983)

It can be difficult to comprehend the meteoric rise of Eddie Murphy’s career. He was only 19 when he became the breakout star of SNL‘s 1980 season. Within two years, he’d released his first film, sometimes credited as the first buddy cop film, 48Hrs. The year after that, he released his seminal standup special Delirious, and his much-anticipated sophomore outing, Trading Places.

Effete Richy-rich Louis Winthorpe (Dan Aykroyd) is the victim of a switcheroo by his stodgy old bosses at the commodities exchange firm Duke & Duke, who bet that streetwise con artist Billy Ray Valentine (Murphy) could perform equally well in his position. Jamie Lee Curtis rounds out the cast as Ophelia, the sex worker who takes pity on Louis once he’s tossed out onto the gutter. Once they discover they’ve been played, all three team up to get revenge on the Duke boys.

Aykroyd gleefully skewers the Hyannis Port WASP experiencing his first taste of the real world, and Murphy places himself in the running for best look directly into the camera, a good 30 years before The Office. The film does contain some dated tropes and most broadcasts you’ll find are marked with disclaimers to that effect, but for those willing to accept it as a product of its time, Trading Places remains one of the finest comedies ever put to film.

Rent it on Amazon Prime Video

7 Tootsie (1982)

One of the more dramatic entries on this list, Tootsie is so structurally perfect that it joins Chinatown and Star Wars – Episode IV: A New Hope as one of the scripts most often referred to in screenwriting manuals.

While we follow gifted actor Michael Dorsey in his misguided attempt at fame by transforming himself into a middle-aged woman, both the dramatic and the comedic feelings come from a very real place. The cast of characters surrounding him— Sydney Pollack as his tut-tutting agent, Teri Garr as his sometimes-girlfriend, and a revelatory Bill Murray as his cynical roommate— all come together to make a hilarious and far-fetched premise into a believable and heartfelt film.

It’s rare that a comedy should be recognized at all, but Tootsie was nominated for no less than ten Academy Awards, including a win for Jessica Lange as for Supporting Actress, as Michael’s coworker crush. Truly, one of the most successful classics of American comedy that everyone should see at least once.

Stream it on Paramount+

6 Annie Hall (1977)

Annie Hall is the quintessential Woody Allen romantic comedy, about a neurotic comedian, Alvy, reflecting on the details that led to the failure of his relationship with Annie.

Allen’s distinctive style is on full display. He breaks the fourth wall, disseminates traumatic sections of his youth, meticulously dissects the metacommunications of simple flirting, experiments with drugs and sex, and submits his characters to the kind of shame, lonesomeness, and desperation that has you longing to call your ex in the middle of the night, even when you know better.

Allen himself plays his usual self-loathing writer, complete with a play-within-a-play dramatic scripting of his relationship, and Diane Keaton plays arguably her most famous role in a career filled with bangers. While Allen himself wouldn’t discount his own romantic neuroses, Annie’s hangups about sex, art, and love are hardly made of delicate crystal; no one is innocent in the crime of love.

The narrative devices are incendiary and revolutionary, and the chemistry between the leads is sublime, garnering Keaton a Best Actress Oscar, as well as Best Original Screenplay, Director, and Picture for Woody.

Stream it on Max

5 Life of Brian (1979)

Life of Brian is the movie that was independently financed by former Beatles guitarist George Harrison, simply because he wanted to watch the movie. Monty Python had already made a name for themselves at BBC when they invented modern sketch comedy with Flying Circus. By ’75, they’d achieved international fame with Monty Python and the Holy Grail. When it came time to ridicule the New Testament, it was difficult to find backers for the touchy subject.

Related: Monty Python: Every Movie, Ranked

In and of itself, the plot of the film rarely pokes fun at the Christian messiah themselves, but rather at the diabolically ignorant individuals, and sometimes well-intentioned mobs, that make hay of dogma. That everybody is worshiping a reluctant fraud named Brian, who happened to be born next door to Jesus, is probably the most flagrantly antagonistic part of the movie. But it’s so silly that, despite the parody, you’re mostly laughing at the boys’ voices while in drag and harmlessly purile gags like “Biggus Dickus.”

Stream it on Netflix

4 National Lampoon’s Animal House (1978)

Is there a more bawdy, sure-to-offend, gratuitous, misogynistic, subversive, and downright immoral comedy in all of cinematic history than Animal House? If so, then it deserves a pledge pin on its uniform.

Promoting, and in some cases inventing, college comedy-staples like food fights, toga parties, and road trips, the sexual predators of the Delta frat house regularly get drunk, cheat, lie, steal, and shame themselves through classes at the fictional Faber College (motto: “Knowledge is Good”). It’s an exaggerated amalgamation of the college lives of its writers, no doubt combined with a few “did you hear about the guy who” fables.

In no particular order, it features acts of animal cruelty, recreational drug use, debilitating alcoholism, wanton violence, manipulating and lying to women to get dates, and a particularly troubling almost-statutory rape. It’s hardly for consumption by a modern woke crowd, but the bad guys at the rival Omega house, and a vengeful dean, are so smarmy and smug, it makes you want to laugh and cheer all the more at the antics of the dirtbags over at Delta.

Not for the feint of heart, Animal House will make you wonder about your goody-goody boomer relatives with a little more suspicion, wondering just exactly what college life was like back then.

Stream it on AMC+

3 This is Spinal Tap (1984)

This is Spinal Tap was the first of several movies to follow Christopher Guest’s unique method of capturing comedy: film hours and hours of hilarious professionals improvising, and cut the footage together to get a movie. He would use it again to great acclaim in Waiting for Guffman and Best in Show. Fans of Guest will still argue over which is best.

The first film directed by Rob Reiner, whom everyone still knew as Meathead from All in the Family, this mockumentary follows a fictional British metal band called Spinal Tap. The standout feature of this genius film is in its dry humor, salty and aged like a Jamón Ibérico, with double the ham. The silliest stuff comes out of the mouths of its stars, but they believe it one hundred percent.

It’s the comedic forebearer for modern ticklers Arrested Development and Curb Your Enthusiasm, to name a few. In fact, it’s difficult to find a comedy writer who doesn’t hold some kind of reverence for This is Spinal Tap.

Stream it on PlutoTV

2 Airplane! (1980)

Humor is subjective, and there’s no true metric for what makes a film a once-in-generation comedy. But the winner of the highest volume of gags, by far, is the 1980 disaster film parody masterpiece Airplane! It was even calculated officially by Forbes.

“This woman has to be gotten to a hospital.”

“A hospital? What is it?”

“It’s a big building with patients. But that’s not important right now.”

It’s the rare movie whose humor is so infantile, so ridiculously childish, it makes it funny at any age. It’s rapid-fire sketch, physical comedy, brilliant acting, wordplay, and a sight gag for practically every scene in the movie.

It’s the kind of dumb that only really smart people can come up with, and the story is so stupidly simple that if you’re paying attention to the undertones of the plot, you’re watching it with the wrong intentions.

Stream it on Paramount+

1 Blazing Saddles (1974)

Any time someone tells you that modern comedy can’t get away with what it used to, they’re talking about Blazing Saddles. Comedic geniuses Mel Brooks and Richard Pryor team up to tell the story of a Black man appointed sheriff of Rock Ridge, a frontier town in the Old West.

“You’ve got to remember that these are just simple farmers. These are people of the land. The common clay of the new west. You know — morons.”

Stars Cleavon Little and Gene Wilder have immediate chemistry, Harvey Korman is underappreciated as the debutante bureaucrat with a fiendish plot, and Madeline Kahn steals the show in about ten minutes of screentime, as usual. The dialogue is in the vernacular of the time, and race is the central theme, so there’s pretty indiscriminate use of the n-word in this one. Along with just about every other racial slur. It’s indefensibly hilarious.

Stream it on Paramount+