Sketch comedy has changed a lot since its vaudeville days.

Once confined to a stage, sketches unleashed themselves on our big glowing boxes (TVs) before lying in wait on the Internet, ready to be summoned at any moment on our smaller glowing rectangles (phones).

The past two decades have been especially defining for the medium. The Internet, social media, politics, social mores, and public discourse on race and gender have altered dramatically; sketch comedy has not only reflected that, but has also helped propel those changes forward.

I set out to make a list of 20 defining sketches that captured this sea change, starting with the year 2000. For the purposes of this list, “defining” does not mean the “best” sketches, or even objectively funny ones. What we find funny rapidly evolves, and not all jokes can stand the test of time.

“Defining” can be a nebulous descriptor, but let’s try to give some form to it: Which sketches helped alter sketch comedy itself? Which exemplified or popularized a certain kind of comedic sensibility? What permeated our shared psyche or charted a new way through changing media?

To qualify, here are some ground rules: Sketches had to involve characters in a short vignette that was written and plotted out, rather than improvised. They must have been televised. (Sorry, I’m not combing through the graveyard of Vine for content to judge.) They had to come from American shows.

The final list, which is in no particular order, includes sketches you’ve seen, ones you haven’t and a lot of “Saturday Night Live” — the natural outcome of being the longest-running and most widely watched sketch series. Yes, your favorite bit may be missing.

Throughout comedy’s evolution, sketches have held a prominent place within our culture. They can still give us a new shared language for the mundane. They can allow us to process the serious or painful aspects of our existence. Or, they can simply make us laugh.

Note: Some of the clips include vulgar language and content.

SNL

“More Cowbell” (2000)

If we had to explain to future generations how things went “viral” before that word was associated with anything but a contagious disease, we might point to this 2000 SNL sketch about Blue Oyster Cult’s “(Don’t Fear) The Reaper.” It’s very weird and non-topical, but it somehow managed to infect us all. For years after, its legacy followed around the real-life band, who had to deal with fans at shows yelling for more — ha ha, get it! — cowbell. Will Ferrell’s physical comedy — his too-small shirt creeping up his belly as he wildly struck his humble instrument — and Christopher Walken’s, well, Walken-esque delivery may have sold the sketch. However, two lines in particular — “I need more cowbell” and “I got a fever, and the only prescription is more cowbell!” — took over our brains and still hasn’t let go. (People are still out here in 2019 putting “cowbell” jokes on their dating profiles.) Somehow, we all knew to laugh at this, tell each other about it and repeat the lines over and over, without the digital public square of Facebook and Twitter.

To watch the sketch, click here.

SNL

“Lazy Sunday” (2005)

This music video may be more Weird Al than classic sketch comedy, but what “Lazy Sunday” accomplished secures its place on this list. When the rap by Andy Samberg and Chris Parnell first aired in 2005, TV was still being made with just TV in mind and YouTube was but a few months old. Their “digital short” first blazed what is now a well-worn path for sketch comedy, becoming one of the first bits from television that found a second life online, amassing millions of views within days. After NBC raised a fuss to get the YouTube clip taken down, people posted ripped versions. Regular people made their own parody versions in a harbinger of viral challenges to come. “Lazy Sunday” was asking for it: Its hardcore beat and lyrics that so ludicrously contrast with a sweet premise (how to enjoy a lazy Sunday) were irresistible. “The Office’s” Michael Scott even made his own Scranton, Pa.-specific version.

“Lazy Sunday” also raised the profile of comedy-factory the Lonely Island (made up of Samberg, Jorma Taccone and Akiva Schaffer), and set a precedent for infectious SNL song parodies that became instant viral sensations, such as the Emmy Award-winning “D--- in a Box” and the rap Grammy-nominated “I’m on a Boat.”

To watch the sketch, click here.

“Chappelle’s Show”

“Frontline — Clayton Bigsby” (2003)

Dave Chappelle’s presentation of a black white supremacist remains a fixture of popular culture, still embedded in our public consciousness more than 15 years after it first aired. When Spike Lee first heard the pitch for “BlacKkKlansman” — the 2018 movie based on a real story about a black cop infiltrating the Ku Klux Klan in the ’70s — he thought it was a remake of the sketch.

“Clayton Bigsby” was inspired by a different, real event as “Chappelle’s Show” co-creator Neal Brennan has previously explained: After the assassination of Martin Luther King Jr., Chappelle’s mixed-race, blind grandfather boarded a bus in Washington, a city that was engulfed with riots. Chappelle’s grandfather overheard passengers talking about beating up a white guy before he realized: Oh wait, I’m that white guy. The notion of a black man unaware of his blackness was then taken to its extreme on the first episode of “Chappelle’s Show.”

The premise is outrageous, as Chappelle plays a blind, black KKK member who thinks he is white. The n-word is said by white people — repeatedly. There are layers of jokes and an unforgettable exploding head. When Chappelle introduced the sketch on air, he told the audience that a friend had already watched it and said it set back the progress of black people. Chappelle laughed about it then, but it was, and remains, a complex question: How does one consider the audience when walking the line between skewering and perpetuating racism? It is a question that would also be at the heart of Chappelle’s decision a few years later to walk away from the wildly successful Comedy Central series.

To watch the sketch, click here and here.

“Key & Peele”

“Obama’s Anger Translator” (2012)

President Barack Obama brings out actor Keegan-Michael Key from "Key & Peele" to play the part of Luther, the president's "anger translator," during his remarks at the White House Correspondents' Association dinner in 2015 in Washington. (Evan Vucci/AP)

SNL usually leads the pack for political sketch comedy, but it didn’t do many memorable pieces during the Obama presidency. “Key & Peele,” however, peppered its shows with some of the most cutting and unique societal commentary during the era of the first black president, including the “Anger Translator” sketches.

The recurring sketch featured Jordan Peele’s “no drama Obama,” as he was called during his presidency, having to keep his cool in public, so he enlists the services of an anger translator, Luther (Keegan-Michael Key). When people such as Donald Trump circulated the conspiracy theory that Obama wasn’t born in the United States, or when Rep. Joe Wilson (R-S.C.) yelled “you lie!” during Obama’s State of the Union address, the real-life Obama “couldn’t come off like an angry black man, especially early on, so what Luther says are things that ring true to us, and we felt like we were giving the truth a voice in a lot of ways,” Peele explained to NPR in 2013.

Every sketch features Peele’s pitch-perfect Obama impression, calmly discussing the matters before him, and then Key’s Luther yells and lets loose. Luther punctuated pivotal moments in Obama’s presidency, such as in a victory sketch that was posted online before Mitt Romney uttered a word of his concession speech. Luther also stood alongside the real Obama as he gave a speech at the White House correspondents’ dinner in 2015.

To watch the sketch, click here.

“Chappelle’s Show”

“Charlie Murphy’s True Hollywood Stories — Rick James” (2004)

This sketch did many things. It put “Chappelle’s Show” on the map; revived Rick James’s career, giving him newfound relevance after years away from the spotlight; and spawned a catchphrase that would dog Chappelle for years. The comedian heard, “I’m Rick James, bitch!” everywhere, with hecklers ruining his stand-up performances and even family trips. (During a visit to Disney World, people bombarded Chappelle with the phrase. “Hey man, hey,” Chappelle quipped during his 2004 stand-up special. “You mind not calling me a bitch in front of my kids?”)

The sketch was silly and unpredictable, featuring Charlie Murphy telling an apparently true story about partying with the singer in the 1980s. (Murphy also told a story about Prince in a different memorable sketch.) Chappelle portrayed an outrageous young James, and the “Super Freak” himself gave his side of the events and described his behavior with a now-classic line: “Cocaine is a hell of a drug.”

To watch the sketch, click here and here.

SNL

“Debbie Downer” (2004)

It can feel cheap to get laughs from breaking in a sketch, as Liz Lemon explains on “30 Rock,” but sometimes the chaos of seasoned performers breaking so intensely can be transcendent. Rachel Dratch introduced us to her Debbie Downer character in this sketch, which made a murderers’ row of comedians laugh so severely that there was no use in hiding it. Horatio Sanz used a waffle to wipe away his tears. The cast reportedly didn’t know there would be a sad trombone sound after Debbie said super depressing stuff, which is what kicked off the cascade of onstage laughs. What followed from that moment felt like a shared experience between cast and audience, one that’s just as resonant today as it was when it first aired. “I still believe that sketch may be a cure for low-level depression if watched regularly,” Amy Poehler, one of its stars, wrote in her autobiography.

To watch the sketch, click here.

SNL

“Black Jeopardy With Tom Hanks” (2016)

Making funny and unique political sketches during Trump’s campaign and presidency has been a challenge: The humor is often predictable, and the subject matter of the jokes, fleeting. This edition of “Black Jeopardy,” which aired on the eve of the 2016 presidential election, stands as one of the best examples of recent political sketch comedy.

The fake game show quizzes contestants on aspects of black culture. In this version, Tom Hanks plays a rural, white, MAGA-hat-wearing voter, and to the surprise of everyone, turns out to have a lot in common with the two black contestants on the show. The sketch managed to offer timely, funny and incisive political commentary without a single Trump impersonation, and it spawned think-pieces about how voters are depicted by the media. “It had more to say about class and race than a thousand tenderly crafted portraits of the white working class,” wrote one prominent political columnist. It also achieved another rare feat in a hyper-polarized time: Both conservatives and liberals found it funny.

To watch the sketch, click here.

“MADtv”

“Ms. Swan” (2002)

No one is really basking in “Ms. Swan” nostalgia. These days, the sketches featuring the recurring character mostly get sent around to prove a point about the kind of “problematic” stuff TV networks used to air.

Fox’s “MADtv” tried to give “Saturday Night Live” a run for its money by showcasing a different kind of comedic taste. It had a more diverse cast than SNL, and it focused heavily on pop culture parodies. The “Ms. Swan” sketches, among the most widely remembered of “MADtv’s” work, were also a harbinger of future debates over comedy and representation. (Sound familiar?)

Alex Borstein, who has Hungarian, Mongolian, Russian and Polish roots, wrote in a Los Angeles Times op-ed that her character, who hailed from the fictional country of Kuvaria, was based on her own “spunky” grandmother, “an immigrant who toys with her ability to speak and understand English as it suits her.” Ms. Swan was “an amalgamation of many nationalities,” but many people saw, and still see, Ms. Swan as a stereotypical Asian lady with an exaggerated accent — an example of the sort of “edgy” comedy from the early aughts that more overtly trafficked in racial stereotypes.

To watch the sketch, click here.

“Kroll Show”

“Too Much Tuna” (2013)

John Mulaney and Nick Kroll on "Kroll Show." (Luke Fontana) (Luke Fontana)

Like starting a food truck before opening a restaurant, a comedy sketch can be a manageable testing ground for a much grander pursuit. The comedy sketch to movie evolution has been done over and over, but the sketch to Broadway performance to Netflix special? “Too Much Tuna” blazed a different kind of path. Nick Kroll and John Mulaney had performed as Gil Faizon and George St. Geegland around New York before, but “Kroll Show” brought the septuagenarians’ fake public-access prank show before a national audience. The platform gave the duo enough juice to sell out a five-month run of their play, “Oh, Hello on Broadway.” That production also helped Mulaney rebound after his failed sitcom: He’s now a bigger star than ever, selling out a week of shows at Radio City Music Hall and winning an Emmy for his acclaimed “Kid Gorgeous” stand-up special.

To watch the sketch, click here.

“Inside Amy Schumer”

“Last F---able Day” (2015)

(for The Washington Post)

Sometimes a sketch is the best vehicle to articulate a phenomenon that’s so pervasive and long-standing that it’s just the wallpaper to our culture. Amy Schumer managed to nab three massive stars to play themselves in this sketch, and each delivers a pitch-perfect performance. Tina Fey, Patricia Arquette and Julia Louis-Dreyfus have all gathered in a picturesque meadow to celebrate the last day “Veep” star Louis-Dreyfus is considered romantic-lead material by the entertainment industry. “You know how Sally Field was Tom Hanks’s love interest in ‘Punchline,’ and then like 20 minutes later, she was his mom in ‘Forrest Gump?’ ” Louis-Dreyfus notes. The women let loose, both figuratively and literally (yes, there is a fart), as they joke about ageism and the double standard that women in Hollywood face. Remember, this was before #TimesUp inclusion-rider Oscar speeches.

To watch the sketch, click here.

“Key & Peele”

“Substitute Teacher” (2012)

This sketch, which almost became a movie, helped secure “Key & Peele’s” place as the purveyor of outlandish yet relatable and subversive comedy. Key’s Mr. Garvey, an instructor from the inner city who is a substitute teacher in an all-white classroom, is a flip of the white-teacher-inner-city classroom trope. Mr. Garvey has trouble taking attendance with ridiculous, hard-to-pronounce names such as “Aaron” and “Blake.” (“A-a-ron, where are you?”) The comedy duo hadn’t planned to post the sketch online for whatever reason, but it blew up when they did. The sketch is highly quotable, having a substitute teacher is a universal experience, and it’s the perfect clip to send to anyone who has one of the names Mr. Garvey butchers. Seven years later, the humor still holds up, and “Substitute Teacher” stands as Comedy Central’s most-viewed YouTube video, amassing some 175 million views and counting. As Peele said in an interview with the Week, “It’s taught us a lot about how the Internet works.”

To watch the sketch, click here.

SNL

“First Presidential Debate: Al Gore and George W. Bush” (2000)

Election years are SNL’s bread and butter. The sketch show has a long, storied history of shaping the public perception of various political figures. Perhaps nowhere did that happen more than with George W. Bush and Al Gore, specifically with this sketch. The spoof of their presidential debate set the stage for Will Ferrell’s impersonation of Bush as a dimwitted yet lovable guy that many have argued made the real Bush much more likable. After it aired, cable news programs replayed the sketch over and over, multiplying its effect: Gore’s aides reportedly showed him Darrell Hammond’s portrayal to help the vice president for his second debate, and a senior adviser has said the sketch hurt Gore’s campaign. While the references may be dated now, the terms the sketch birthed — “strategery” and “lockbox” — still get bandied about in political analysis.

To watch the sketch, click here.

“Key & Peele”

“Continental Breakfast” (2013)

(For The Washington Post)

This sketch gives us a glimmer of the genre-bending that was to come from Peele, a sketch comedian who would go on to win an Oscar while reviving horror as a prestige genre and sparking a conversation over what makes a comedy a comedy. In it, a traveler rabidly enjoying a complimentary continental breakfast goofily indulges in muffins, cereal and yogurt, backed by the music of Strauss, and exclaims, “I love being in continent!” It could have ended on the pure joy, but it takes a hard turn. Peele’s character eventually breaks into tears and the bit ends on a spooky note, with a callback to the final scene in “The Shining.” (It also hints at themes of psychological imprisonment, potentially an early iteration of the “the sunken place” that would be explored further in “Get Out.”) The old-timey photograph shown at the end of the sketch would later hang in Peele’s offices. And, after making hundreds of sketches, winning prestigious awards and making two films, it is this photograph — specifically, the close-up of Peele’s frozen-in-time character — that is his Twitter avatar, serving as his public face to the world.

To watch the sketch, click here.

“I Think You Should Leave With Tim Robinson”

“Focus Group” (2019)

It would seem that streaming services, without the same kind of time and content limitations as regular TV, would be perfect for sketches, but few have risen above the fray and turned into mini pop-culture wonders. Enter the “Focus Group” sketch, a prime example of how sketch can thrive in a post-cable and network TV world. The premise: A focus group brainstorms their dream features for a car, during which an older male participant keeps hammering his point: The car should have “a good steering wheel that doesn’t fly off while you’re driving.” He’s totally out there, with a distinct haircut (bald, but with long hair?) and an accent that’s difficult to place. But the sketch takes an unpredictable turn away from “here’s a weird guy with bad ideas” when the others in the focus group stop reacting to him like he’s crazy and join him in making fun of another guy, Paul. What is this sketch even about? Who cares. It’s so zany and delightful, with a plethora of memorable sound bites (“I think it’s a good idea and I stand by”) that can be adapted to numerous scenarios — and, fittingly, have been turned into a bunch of memes.

To watch the sketch, click here.

“Inside Amy Schumer”

“12 Angry Men Inside Amy Schumer” (2015)

It seems a distant memory, but Schumer’s show — which came before she turned into a movie star and a somewhat divisive celebrity — was highly celebrated, and this episode-long sketch shows why. The highly stylized black-and-white parody spoofs the 1957 courtroom drama“12 Angry Men,” except in this case, the jurors have to decide whether Schumer is hot enough for TV. The sketch has so many stars in it that just as you get a handle of your shock over one (Jeff Goldblum), here comes another (Paul Giamatti). The cinematography is excellent, and John Hawkes delivers an award-worthy acting performance as he makes serious arguments and slowly convinces his fellow jurors that Schumer, indeed, is hot enough. Along the way, we get to hear jokes about the double standards women encounter. The entire sketch was a risk — how many Comedy Central viewers have even seen the movie? — but the attempt at high lowbrow humor became a big hit. And for this season, Schumer would go on to win the Emmy for outstanding variety sketch series in the first year of the category.

To watch part of the sketch, click here.

“The Amanda Show”

“Judge Trudy” (2002)

Amanda Bynes as Judge Trudy on "The Amanda Show." (Nickelodeon)

Sadly, because of the time parameters we set, most sketches from the iconic children’s show “All That” don’t qualify for this list. So, we’ve reserved this spot for one of its inheritors. “The Amanda Show” was among a slew of sketch comedy series that starred and targeted kids. At the time, Amanda Bynes was considered a comedy prodigy, and her “Judge Judy” parody sketches always ended with a bizarre, out-of-nowhere twist: dancing lobsters. It’s so out there and incongruent with the rest of the sketch, but it must have seeped into a young generation’s comedic temperament. We see it today via the absurdist, nihilistic humor millennials use on Twitter. Those dancing lobsters were the prelude to the break-dancing hot dog hanging with Soviet-era icons.

To watch the sketch, click here.

“Chappelle’s Show”

“The Racial Draft” (2004)

This sketch first aired in 2004, but the premise — that races could have delegations draft new members for their groups, much like in the NBA or NFL — still resonates, as every so often, the joke comes back up on social media as people argue over fictional trades. During the seven-minute Chappelle sketch, Lenny Kravitz is drafted by the Jewish delegation, Tiger Woods gets drafted by the black delegation and the same representative gives away Condoleezza Rice to the white team. There are cameos from “Chappelle’s Show” favorites Mos Def (now known as Yasiin Bey) and the Wu-Tang Clan, who get drafted by the Asian delegation. It’s outrageous and silly, but it’s also a cutting examination of racial identity.

To watch the sketch, click here.

“Portlandia”

“Put a Bird On It” (2011)

(For The Washington Post)

One of the clearest signs that a comedy sketch has made a dent is when people start saying its signature line. Fred Armisen and Carrie Brownstein turned the mundane into the magical by simply slapping images of birds on various objects and exclaiming, “Put a bird on it!” After this, you saw bird patterns on dresses (and “Portlandia” references) everywhere as the show became a pioneer in how to make fun of distinct “hipster” habits. The vibe of this sketch, which aired in the show’s first episode, would set the tone for how the series approached comedy: with highly specific settings and characters who seemed normal but turned weird, all of whom were recognizable to you — even if you had never been to Portland and asked about farm-raised chicken.

To watch the sketch, click here.

“Robot Chicken”

“The Emperor’s Phone Call” (2013)

“Robot Chicken” emerged during that strange time when entertainment companies were figuring out how to make TV for the Web. Sony’s Web streaming service, Screenblast.com, developed and first aired the stop-motion sketch series. Adult Swim picked it up, turning it into one of Cartoon Network’s staple programs and, eventually, into one of its longest-running shows. The series specialized in skewering pop culture and indulging in more nostalgic touchstones, such as in this particular Star Wars sketch, which is among its most widely known. In it, Darth Vader calls Emperor Palpatine to report that the Death Star has been destroyed, and Palpatine is just an exasperated boss who puts Vader on hold so he can order a turkey club for lunch. Star Wars creator George Lucas saw the sketch, and two years later, LucasFilms participated in an entire episode dedicated to the space franchise, involving the real-life Lucas as well as Luke Skywalker actor Mark Hamill; it was nominated for an Emmy. The entire series showed that Internet sensibilities could be adapted for a regular TV audience, who would, in turn, memeify televised sketches.

To watch the sketch, click here.

SNL

“Sarah Palin and Hillary Address the Nation” (2008)

So much of comedy is about timing. When all of the stars align so perfectly, you end up with this sketch. Alaska Gov. Sarah Palin (R) and “Saturday Night Live” maven Fey had two very different lives until they intersected in this sketch, for which Palin — I mean, Fey — won an Emmy. Yes, it’s uncanny that Fey is essentially Palin’s doppelganger, but the performance went beyond, “Wow, they look alike!” The sketch birthed a catchphrase — “I can see Russia from my house!” — that was, and still is, misattributed to the former Republican vice presidential candidate. (The real-life Palin said, “You can actually see Russia from land here in Alaska, from an island in Alaska.”) The approach of this sketch showed how to poke fun at an unconventional candidate. This was a time when repeating a slight variation of a politician’s own words in a comedy sketch was all you needed to do to devastatingly make fun of them. How quaint.

To watch the sketch, click here.

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Editing by Caitlin Moore. Illustrations by James Fosdike for The Washington Post. Design by Joanne Lee.