This week’s question comes from reader Daniel Flight:
“I’ve always wondered what people thought the funniest five minutes of whatever are, be it movie, TV, or book. For me, it’s the scene in Wedding Crashers where John meets Chazz, because Owen Wilson’s reactions are brilliant. In a book, it’s the part in Confederacy Of Dunces where Ignatius meets the Ladies Art Guild with ‘Twelve (12) Inches Of Paradise.’”
Marah Eakin
There’s a lot of funny stuff out there, obviously, but the first thing that comes to mind for me is Paul Rudd’s cafeteria bit in Wet Hot American Summer where, as lackadaisical camper Andy, he takes a full 60 seconds to clean up a plate he’s thrown on the ground. It’s an insane non-sequitur in a film basically composed entirely of non-sequiturs, and even seeing gifs of the scene can make me dissolve into a fit of snorting giggles. Every single piece of the clip is funny, from Rudd’s face when he takes a drink right at the beginning to the sound his chair makes when he pushes it back. Every time I watch it, I discover a new little Easter egg of weirdness, and that’s saying something, considering it’s 60 seconds that that I’ve probably seen hundreds of times since Wet Hot first hit the world back in 2001. I’d love to know how Janeane Garofalo managed to keep a straight face.
William Hughes
I could fill this whole list with examples from the works of Adam Reed; his tendency to put oddly literate idiots in a room and then increase the tension until they’re screaming nonsense at each other will never stop making me laugh. But there’s a reason Archer elevated Reed from Adult Swim cult star to actual success, and it’s all on the screen in the bomb-disposal scene from the first season’s “Skytanic.” Besides gifting the Archer universe with the snarkily competent Ray Gillette, the sequence hits comic perfection by grounding its rapidly heightening absurdity in what we already know about its characters. It’s not just that Sterling Archer is a dick; it’s that he’s the kind of dick whose weirdly high standards of courtesy means he’ll pause in the middle of a bomb disposal just to spite someone for exhibiting hypocritical radio etiquette. Characters talking past each other is a staple of Reed’s comedy, but the way the scene bases both its punchlines—Archer’s pissily hysterical “M. AS IN. MANCY,” and Lana’s exasperated, helium-defying response—in what we already know about them points to the strengths of the show’s core concept.
Sam Barsanti
Walk Hard is a viciously direct parody of musician biopics, but its funniest scene isn’t when John C. Reilly’s Dewey Cox smashes every sink in an enormous bathroom—one-upping a similar scene in Walk The Line. No, its funniest scene—and probably one of the funniest scenes ever—is when Dewey Cox goes to India and meets The Beatles. The film has an absurd approach to cameos from historical figures, which involves casting famous people who barely look like them and having other characters constantly refer to them by their full names, but the Beatles scene takes it to an extreme. Justin Long’s George Harrison and Jason Schwartzman’s Ringo Starr are pretty funny (the former is just tired of everybody and the latter is a goofy dope), but Paul Rudd’s John Lennon and Jack Black’s Paul McCartney are so purposefully terrible that they loop back around and become brilliant. Throw in Black’s reference to being “the leader of The Beatles” and Rudd pausing to look into the camera when he says “imagine,” and the scene is funny enough that I’ll watch the whole movie for it.
Cameron Scheetz
The underrated gem of the Muppets’ cinematic repertoire, The Muppets Take Manhattan, is chock full of deliriously giddy scenes. From a proto-Muppet Babies musical number (“I’m Gonna Always Love You”) to an amnesia-stricken Kermit becoming another cog in the corporate marketing machine, I could probably argue for most five-minute stretches of the film. That being said, nothing makes me giggle uncontrollably like Miss Piggy’s rollerskating chase scene, followed directly by her big confrontation with Kermit. While spying on Kermit and his “strictly platonic” friend Jenny (yeah, sure, Kermy) in Central Park, Piggy gets her purse snagged by a thief and borrows actor Gregory Hines’ skates to chase him down. The scene cuts quickly between Piggy’s frightfully determined face and wider shots that are so obviously a human woman in a costume that it’s hard not to lose it. Piggy finally nabs the burglar, but then, before there’s time to catch your breath, she runs into Kermit and the two hash it out in hilariously classic Muppet fashion: flailing and screaming at the top of their felt longs. Capping it all off, Hines returns for his skates and immediately gets involved in the lovers’ quarrel: “The huggies! You gave Jenny the huggies?” Together, the scenes perfectly highlight everything that makes the Muppets so endearing: charmingly modest effects, pitch-perfect celebrity cameos, and Miss Piggy losing her shit.
Alex McCown
I interviewed animation filmmaker Don Hertzfeldt earlier this year, which was a great opportunity for me to go back through his work and admire its brilliance all over again. I’m pretty compelled by everything he’s done, from the oldest stuff to this year’s World Of Tomorrow, but there’s something that absolutely slays me every time, and it’s maybe one of the most ridiculous things imaginable. It’s in his collection Rejected, which compiles a few short ads he did for companies that quickly rejected them, and then expands it into an existential crisis about art itself. The very first short always sends me into uncontrollable giggles. It’s just a guy holding a spoon that’s far too big, talking about how it’s much too big. Then a banana enters the frame, and my giggles explode into hysterics. I won’t spoil it, so just watch the first minute and 20 seconds of this video above—it’s still genius, and it still kills me every time.
Kyle Ryan
I have repeatedly asserted the perfect joke—maybe the apex of the series!—lies in “Much Apu About Nothing,” from season seven of The Simpsons. As Apu, in the country illegally and facing potential deportation, shares his deep sadness about leaving what has become his home, Homer responds with pure genius: “Wow, you must love this country more than I love a cold beer on a hot Christmas morning.” It works on so many levels that it’s basically a one-line distillation of the golden era of The Simpsons. It kills me. I want to tattoo it on my body in tribute.
Josh Modell
I’m not an out-loud laugher—it’s extremely rare, even though I love comedy. But I have an incredibly strong memory of watching Zach Galifianakis’ Live At The Purple Onion DVD right around the time it came out, in 2006. My wife and I were at another couple’s house, and the two ladies fell asleep soon after we started watching. My friend Dan was dozing a bit. The movie is part stand-up, part documentary, and, most importantly, part mockumentary about Galifianakis’ made-up twin brother, Seth. The segments featuring Seth being interviewed by NPR’s Brian Unger—clearly improvised, as they’re both about to break half the time—never fail to make me laugh. And it’s definitely not just Galifianakis’ effeminate portrayal of his alternate self that does it; it’s the specificity of his made-up memories, and the underlying anger he feels toward his more successful sibling. Start the video above at around 2:20 for a clip so funny that it honest-to-God brings tears to my eyes every single time I watch it.
Erik Adams
There’s nothing like the giddy energy of a good multi-camera sitcom gag rippling through a show’s entire ensemble, and there’s no multi-cam sitcom gag like the boozy phone call at the climax of The Bob Newhart Show’s “Over The River And Through The Woods.” The sequence relies on some of the show’s greatest strengths, with Newhart doing one of his signature one-sided phone conversations while the band of crazies that make up his friends and clients shout Chinese takeout orders at him. There’s also an added agent of chaos: Alcohol, the cause of and solution to all of life’s hysterically incomprehensible interactions. The round of applause Newhart earns when he hangs up the phone (a few feet off from the hook) is well deserved.
Gwen Ihnat
I may have seen This Is Spinal Tap more than any other movie, and I certainly have it memorized. So it’s astounding to me how much it can still make me weep from laughter. Out of all of my favorite musical numbers, though, nothing tops “Stonehenge.” First: great, fanciful rock song, augmented by hilarious hooded costuming and glittery eyeshadow. David St. Hubbins rips into a riveting guitar riff, augmented by Viv Savage’s keyboard solo. Nigel Tufnel adds a soft vocal bridge, and there’s some inexplicable screaming by bassist Derek Smalls. And then, a slightly large pi symbol comes down from the rafters as the aghast band looks on, and a pair of dwarves dances around it. The ensuing band fight afterward almost rivals the song performance in hilarity: “I think that the problem may have been that there was a Stonehenge monument on the stage that was in danger of being crushed by a dwarf.” Last summer, Spinal Tap was featured in the Chicago’s outdoor Millennium Park film series, unfortunately the night of a fairly solid rainstorm. The worst of the torrent hit right around “Stonehenge,” but instead of running for shelter, I stood there, under a tarp, for the chance to see my favorite five minutes of film on the big screen again.
Mike Vago
It’s one of the chestnuts that often gets dragged out as one of TV’s funniest moments, but damn if it didn’t get that reputation for a reason. The funeral at the climax of “Chuckles Bites The Dust,” the Mary Tyler Moore Show episode often cited as the best sitcom half-hour ever made, is one of those moments that works so completely on every level—writing, acting, character, laughs, and sentiment—it never gets less funny no matter how many times you see it. At the beginning of the episode, WJM’s resident children’s entertainer, Chuckles The Clown, is killed by an elephant while dressed up as a giant peanut. The staff finds this hilarious, but Mary fails to see the humor. A man they’ve all known for years is dead, and she insists that everyone shows respect. The tension between that respect and the absurdity of the situation builds and builds until Chuckles’ funeral, when the seriousness of what happened finally hits everyone—except Mary, who just loses it.
Drew Fortune
For me, golden era The Simpsons (generally regarded as seasons two through nine) continually rewards, mining a 22-minute runtime for optimal laughs. Three-second establishing shots sometimes yield the biggest laughs for me (I think of Pay & Park & Pay every time I enter a parking garage). But my favorite protracted sight gag is Sideshow Bob’s ill-fated car undercarriage ride in the season 5 classic “Cape Feare.” Affecting DeNiro’s psychopath Max Cady but lacking all menace, Sideshow Bob is treated to a silent era-esque cavalcade of calamity as he straps himself under the Simpsons’ family car for a journey to Terror Lake. During the short trip, he is pummeled repeatedly by road bumps, driven through cacti, scalded by Homer’s boiling coffee, and shortly after trampled by the Terror Lake marching band and its elephants. But, there are also rakes. Lots of them. Besides Bart, rakes prove to be Bob’s arch enemy, and the repeated “thwack” and Kelsey Grammar-voiced grumbling, are 34 seconds of grand idiocy, a throwaway joke that runs the gamut from funny, to annoying, to funny again, and finally to hilarity. The payoff is that the Yale-educated, would-be supervillain extraordinaire Bob is subjected to such slapstick misfortune, when he should be rowing against Princeton to victory, or at least successfully killing Bart.
Carrie Raisler
It might be repetitive to choose another David Wain/Paul Rudd collaboration, but I can’t not answer with Paul Rudd’s dirty mirror monologue in Wanderlust. There’s something absolutely magical about the juxtaposition of Rudd’s innocent face with all of the ridiculously awkward, dirty things coming out of his mouth, made perfect by adding the most over-the-top Southern accent of all time. It doesn’t hurt that within the context of the film, that scene almost comes out of nowhere, like a strange little comedy gift in the middle of a film I was only mildly amused by otherwise. I laughed so hard in the theater tears were literally rolling down my face, and the moments were Rudd almost breaks before reining it back in make subsequent watches just as hilarious. The word “dick” has never been so funny.
Kate Kulzick
A lot of TV’s funniest moments fall into either the 30-second or 10-plus minute designations for me, so I’m going with a moment from film that breaks me every time I see it: “Springtime For Hitler” from The Producers (1967). Throughout the film, producers Max Bialystock and Leo Bloom strive to put on the worst, most offensive show in history, a loving tribute to Adolf Hitler. When we get to opening night and finally see the first number, the show absolutely delivers. What sells the sequence, along with the reaction shots of the stunned audience and delighted Bialystock and Bloom, is its warm embrace of Broadway spectacle. The cast are all broad smiles and crisp diction and the full orchestral score adds energy and authenticity to the performance. From the excited, Sound Of Music-esque opening to the parade of hilariously costumed showgirls to the goose-stepping chorus line, the sequence builds and builds, growing increasingly over the top and ridiculous until the piece de resistance—where I always lose it—the spinning swastika. The number commits fully, a hilarious payoff to the first two acts of the film, and no matter how many times I watch it, I always laugh as hard as I did the very first time I saw it.
Noel Murray
Lately, Ricky Gervais seems to be relying almost exclusively on the braying, obnoxious side of his comic persona, which is a shame, because in The Office and Extras he was always funniest when his characters were stuck in ridiculously humiliating situations, and having their will slowly sapped. The Extras scene that slays me every time comes in series two, when Gervais’ Andy Millman has become a sitcom star, in a show he hates. While trying to explain his situation to David Bowie in a pub’s pathetic “VIP area,” a sudden burst of inspiration sends the pop star to the piano, where Bowie composes a song about what a sellout Andy is. The only thing funnier than Gervais’ increasingly hangdog expression as The Thin White Duke coaxes an entire room to sing about the “chubby little loser” who “sold his dream” is how carelessly cruel Bowie is in describing Andy’s excessive weight and low intelligence. He takes a bad situation and keeps making it worse and worse.
Will Harris
I’m sure I could produce dozens of answers to this question and not feel bad about submitting any of them, but I’m going with a moment from a true Hollywood classic: the passport scene from the Marx Brothers’ 1931 film, Monkey Business. After stowing away on an ocean liner, the boys find themselves stuck without a way to get past a passenger checkpoint, but when Zeppo miraculously produces Maurice Chevalier’s passport, each of them takes a shot at using it by performing “You Brought A New Kind Of Love To Me.” I don’t know if there’s another scene in the entire Marx Brothers canon that so perfectly sums up the abilities of Chico, Groucho, Harpo, and Zeppo in such a succinct fashion, but I do know that it never fails to make me laugh.
Jesse Hassenger
I’m grateful to Drew and Kyle taking a Simpsons bit, to free me from the burden of trying to figure out which five-minute segment somewhere in season four or five best applies as the true answer to this question. Instead, I’m going to also go with something Muppets-related that I don’t think steps on Cameron’s toes. While I love the actual Muppets dearly (they were probably the first bit of pop culture to really crack me up), I’m not sure if I’ve ever laughed harder than I did while watching the mysterious YouTube creations known as the Tiny Fuppets. I’m a sucker for any jokes involving low-rent and/or poorly translated knockoff properties and the flawlessly executed idea of a Portuguese Muppet Babies ripoff is pretty much engineered to destroy me with laughter. To get my approximately-five minutes I’d point particularly to “Summer Splash” and “A Modest Wish” because the first time I saw these two segments back to back, I had to pause them. I was legitimately afraid I might pass out.
Dennis Perkins
From his first days on SNL to present-day mega-stardom, Will Ferrell never shows up to a talk show empty-handed. Seemingly averse to the usual movie-promotional chit-chat, Ferrell always comes to play, usually with a funny, strange conceptual comedy bit under his arm, none more brilliant than his 2002 appearance in character as Robert Goulet on Late Night With Conan O’Brien. Following up on his then-recent Goulet SNL sketch—where his version of the perpetually out-of-touch crooner dropped a very ill-considered rap album—Ferrell sweeps onto the set as Goulet, upping the ante of his subject’s boozy, Las Vegas schmoozing to delirious heights. From consistently mistaking Conan for Carson (“Burbank!”), to reminiscing about the sexy dames he imagines he saw in Johnny’s green room (“Dyan Cannon—she’s got a shape to her”), to breaking out into inexplicable hostility (“I’ve choked bigger men than you!”), to getting lost in the middle of his decidedly un-requested rendition of “My Favorite Things,” it rapidly becomes apparent that Ferrell’s Goulet is the only guest Conan’s getting that night. The way that the audience intermittently lapses into confused lulls, only to be jump-started into helpless laughter by the singer’s catchphrase (“Goulet!) is echoed by O’Brien, who can barely keep it together. At the time, I was certainly a fan of Ferrell’s, but this sustained, lunatic appearance cemented him in my mind as one of the funniest bastards I’d ever seen.
Caroline Siede
With so much ironic comedy floating around these days, it’s easy to forget how funny earnestness can be. Take for instance the vastly underrated Romy And Michele’s High School Reunion, which features my all time favorite comedic set piece: A bizarre dance sequence set to Cyndi Lauper’s “Time After Time” that’s played as if it’s the most normal thing in the world. When billionaire Sandy Frink (Alan Cumming) asks former high-school outcast Michele (Lisa Kudrow) to dance, she requests that her best friend Romy (Mira Sorvino) join them. The trio immediately improvises a strangely beautiful interpretive performance that’s all the more funny because no one feels the need to comment on how weird it is.
Kayla Kumari Upadhyaya
I’ve always been a sucker for a strong cold open, but especially a strong, chaotic cold open. And in this admittedly specific category, there is one chaotic cold open that stands out above them all: the first five minutes of The Office’s “Stress Relief Part 1.” Dwight stages a fake fire in order to teach his fellow Dunder Mifflin employees an important lesson about office safety. Being Dwight, he takes the simulation a dozen steps too far, and madness ensues as everyone becomes convinced they’re going to die in their least favorite place on the planet. The chaos is perfectly staged from start to finish, but the part that pushes me over the edge is when Angela pulls a full cat out of her filing cabinet and throws him up to Oscar, who is making his escape attempt in the ceiling, only to have Bandit the cat come crashing back down through the plaster. Nothing quite compares to how I reacted when I first watched the episode during airtime, following the 2009 Super Bowl, when I very literally ended up rolling on the floor in a fit of laughter with a group of my friends. But shout the words “Save Bandit!” anywhere in my vicinity, and you might see some tears.
Molly Eichel
I’ve written about this a million times but goddamnit if I don’t always laugh maniacally at the quiz scene in Friends’ “The One With The Embryos.” Part of that has to do with repeat viewings—I tend to watch this episode a lot—and the familiarity I have with all of the characters. But every single time I see this, and it bears repeating that I watch this episode a lot, I crack up. Maybe it’s the incredible chemistry the cast has, or how each role they take on reinforces who they are as characters, or the answers—Viva Las Gaygas!, Weekend At Bernies—or Monica’s reaction when they lose, but I laugh even as I yell out the answers along with the cast.
Nathan Rabin
For some reason, the first scene that sprung into my mind was the glorious sequence in The Big Lebowski where Philip Seymour Hoffman’s unctuous functionary tries to convince Jeff Bridges that the other Lebowski is a pillar of the community and not a pathetic fraud. There’s something about the contrast between Hoffman’s oily artificiality and desperate need to maintain a front and Bridges’ laconic naturalism that is utterly hilarious and of course there is the thrill of watching two of the greatest film actors of all time in their only scene together.
Caroline Framke
I don’t remember what happened the day I saw the episode of television that almost broke me. I only remember that that day sucked. I came home furious and exhausted, probably with a storm cloud over my head à la Eeyore, and collapsed on the couch to catch up on some TV. The first thing I turned on was Parks And Recreation’s fourth-season episode, “The Comeback Kid,” which is a pretty great episode even before the moment that made me forget how much I had been determined to hate that day. The Parks department is trying to help Leslie stage an incredible comeback event for the City Council election. But their collective failures throughout the day bring them to a packed hockey stadium with a tiny stage and about 8 feet of red carpet—on a completely iced-over rink. But the Parks Department is nothing is not determined, and so Leslie bravely leads the way for them to hobble across the ice to the tune of Gloria Estefan’s “Get On Your Feet.” They can’t stop slipping, Ron is carrying a three-legged dog, Chris Pratt is breaking out his best pratfalls, the audience doesn’t know what to do, Gloria Estefan is bravely singing on in a constant loop of that chorus because it’s taking so goddamn long for them to get to the stage, and I lost my mind. I don’t know if I was laughing that hard because it was such a relief not to be in a bad mood or what, but it doesn’t matter. I’ll forever be grateful to those crazy comeback kids.