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).
Thecomediesof 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.
15The Sting (1973)
The second collaboration between stars Paul Newman, Robert Redford, and director George Roy Hill, after 1969’s wildly successfulButch 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 thecoolest pair of actors this side of anOcean’sfilm.
Stream it on The Criterion Channel
14Diner (1982)
The first feature film from director Barry Levinson,Dinercarried 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
13MAS*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’sMASH, 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.
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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 thehorrors 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
12Caddyshack (1980)
Caddyshack
Caddyshackwas 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 toCaddyshack, 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
11Kelly’s Heroes (1970)
There’s not a lot of WWII comedies.Kelly’s Heroesmakes it work. Sure, it stars Clint Eastwood, who finds it difficult to score laughs without an orangutan to lean on (like he did inEvery Which Way But Loose), but the supporting cast pick up the slack.Don Rickles leads the chargeof 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.
10Back to School (1986)
back to school
Back to Schoolwas 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 inCaddyshackandEasy 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
9Harold and Maude (1971)
Harold and Maude
Harold and Maudeis 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+
8Trading Places (1983)
Trading Places
It can be difficult to comprehend the meteoric rise of Eddie Murphy’s career. He was only 19 when he became the breakout star ofSNL’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 specialDelirious, 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 beforeThe Office.The film does contain some dated tropesand 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 Placesremains one of the finest comedies ever put to film.
7Tootsie (1982)
One of the more dramatic entries on this list,Tootsieis so structurally perfect that it joinsChinatownandStar Wars - Episode IV: A New Hopeas 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, butTootsiewas 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 themost successful classicsof American comedy that everyone should see at least once.
6Annie Hall (1977)
Annie Hall
Annie Hallis the quintessentialWoody 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, andDiane Keaton plays arguably her most famous rolein 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.
