OK Boomer, Here Is The Best Comedy Of Your Generation

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OK Boomer, Here Is The Best Comedy Of Your Generation

How does one define something as broad as the comedy of the Baby Boom generation? Don’t sweat it, baby, I got you, says Tony Hendra, the National Lampoon writer/editor who’s probably better known as Ian Faith, the cricket bat-wielding manager of Spinal Tap.

In his curmudgeonly book Going Too Far, Hendra spews nearly 500 pages of teeny-tiny print defining what he terms “Boomer Humor.” But he didn’t need to bother -- he had already accomplished the job in the book’s subhead:  Going Too Far: The Rise and Demise of Sick, Gross, Black, Sophomoric, Weirdo, Pinko, Anarchist, Underground, Anti-Establishment Humor.  

As subtitles go, Hendra’s definition isn’t half bad.  The defining humor of the boomers was anarchist and anti-establishment, especially in contrast to the I Love Lucy and Jerry Lewis laughs that came before it. Just one generation prior, a naughty word or two could get Lenny Bruce thrown in the slammer on obscenity charges.  Fast-forward ten years and George Carlin and Richard Pryor devoted entire concerts to the comic potential of the F-bomb.

Say what you will about the Boomers -- call them self-absorbed, greedy, wasteful, and unconcerned about the depleted world they’re leaving to future generations -- but their comedy was pretty damn good!  With Hendra’s convoluted subhead as a guide, here are ComedyNerd’s picks for the defining comedians, sitcoms, and comedy movies of the Baby Boom generation.

Boomer Comedians

A quick note before we go on -- we’ll define funny people specifically by the era in which they had the most influence, not necessarily by born-on date.  That means comics like George Carlin and Richard Pryor, who were technically born in the final gasps of the Silent Generation, will qualify here since their creative peaks made them Boomer icons. Got it? Let’s go:

Ten Contenders

* George Carlin

* Richard Pryor

* Lily Tomlin

* Steve Martin

* Andy Kaufman

* Gilda Radner

* Jerry Seinfeld

* Robin Williams

* Albert Brooks

* Monty Python

Starting across the pond and then discovered in bits and pieces in America, the too-clever fools of Monty Python exemplified the silly anarchy of their time.  Brooks was the cinema auteur of the Boomer comics, masterminding stupid/smart films like Lost in America and Defending Your Life. He was joined on the big screen by Martin and Williams, two breakthrough stand-ups who maintained that momentum for decades on TV and at the movies. 

Seinfeld may be his generation’s defining sitcom star. Gilda broke through on late night with heartbreaking, hilarious character work, while Kaufman introduced anti-comedy and surrealism to the masses. Tomlin was another brilliant character comic, from Laugh-In to her game-changing 1970s comedy specials to her Tony-winning turn in The Search for Signs of Intelligent Life in the Universe.

But we’re going to cheat here and name co-comedy icons in the Boomer comedian category.  Richard Pryor essentially redefined the form, bringing brutal honesty and aching vulnerability to the stand-up stage. If the Baby Boomers represented revolution -- at least in their younger days before they got so heavily vested in the S&P 500 -- Pryor was its comedy manifestation. No one before Pryor was so frank in discussing politics, race, and social justice.

As for George Carlin? Rarely has a stand-up comic stayed so relevant for decades, not just “popular” in the Bob Hope specials for senior citizens way but in a “he’s still kicking everyone’s ass” way.  We especially like giving him the trophy since he’d likely throw it back in our faces -- no one relished the evisceration of his Boomer contemporaries more than Carlin.

Boomer Comedy Television

Here, we’re not necessarily looking for the best or funniest television shows (‘best’ and ‘funny’ are two great qualities to have, but gold-standard sitcom Taxi, for example, doesn’t feel like it captured the zeitgeist of a generation). Instead, these are our picks for the ten TV comedies that best defined a self-indulgent breed raised on sex, drugs, and rock and roll. 

Ten Contenders

Saturday Night Live


Late Night With David Letterman



The Mary Tyler Moore Show


The Cosby Show

The Larry Sanders Show

The Golden Girls

Golden Girls might seem like the oddball choice here, but its celebration of aging pals who still want to have it all seems … resonant. The same goes for The Cosby Show, a comedy that once seemed progressive and hilarious but has aged as poorly as many Boomers’ politics. 

M*A*S*H and The Mary Tyler Moore Show are both excellent comedies that could only have been made by young Boomers coming into their own.  The shows’ themes -- Single women can have jobs and sex! War is bad! -- seem obvious now but were revelations back in the day.

Late Night with David Letterman, SCTV, and The Larry Sanders Show were the best shows at satirizing television itself, made by the first generation that was raised on it.  The medium had been around long enough to establish tropes aching to be tweaked, and all three did it brilliantly.  

Cheers and Seinfeld both anchored the clean-up spot for NBC’s Must See TV lineups, a slot reserved for decade-defining comedies.  Seinfeld in particular was a cousin to the Letterman and Shandling shows, taking a now mature art form -- the sitcom -- and twisting it into a hilarious pretzel version of itself. 

But the Boomers’ defining television comedy has to be Saturday Night Live, a breakthrough show that started out as a blasphemous, defiant troublemaker, morphed into loud, sweaty, sexist, and obnoxious, and finally settled into a safer, smugger version of its younger self.  Sound familiar?

Boomer Comedy Movies

And once again, not (necessarily) the best comedy movies but the ones we believe best embody all things Boomerdom. 

Ten Contenders

Monty Python and the Holy Grail

The Graduate

Annie Hall

Animal House

A Hard Day’s Night


Blazing Saddles

The Rocky Horror Picture Show

This is Spinal Tap

When Harry Met Sally

Barbarella is a perfect encapsulation of Boomer comedy contradictions--outspoken war critic and feminist icon Jane Fonda takes on an evil scientist in her peek-a-boob latex spacesuit.  And though it may seem like an entirely different kind of movie, The Graduate also exploited the coo-coo-ca-choo of counterculture angst with the promise of weird sex. 

Annie Hall is probably Woody Allen’s best synthesis of lovelorn laughs with psychoanalysis and modernism; When Harry Met Sally is the same movie for Boomers who don’t want to think too hard about the whole business. 

Blazing Saddles tickled the funny bones of Boomers who dared to venture out for a night of risque humor; Monty Python and the Holy Grail did the same thing with an accent.  The Rocky Horror Picture Show took it a step further, providing an actual, lipstick-stained taste of the emerging sexual counterculture. 

A Hard Days Night celebrated the single biggest Boomer influence on popular culture in a surprisingly funny way, then This is Spinal Tap subverted the whole business of rock stardom with a National Lampoon-style slap to the ears.  

But there can be no doubt about the quintessential Boomer comedy movie -- Animal House is literally a movie about an anarchic generation celebrating itself. We’re smarter than the administrators and the cops and the military!  We’re bursting with unbridled sexual energy! We’re thumbing our nose at oppressive authority! NO ONE CAN STOP US!

In addition to somehow being nostalgic for a generation’s “good old days” while it was actually in the middle of them, Animal House was also unbelievably prescient. The film knew exactly what its most outrageous, nonconformist force of nature, one John “Bluto” Blutarski, was destined to become. 

Universal Studios

The filmmakers knew something we didn't. 

 For more ComedyNerd, be sure to check out:

20 Comedy Clichés We’re Totally Over

The Accidental Comedy Career of Tommy Wiseau

15 Viral Videos From The Early Internet That Still Hold Up

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Top image: Special Event Entertainment/HBO

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