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The 17 most awkward moments in TV history

Nose picking on ”Seinfeld,” affairs on ”Sex and the City,” and Diversity Day on ”The Office” are just some of the cringe worthy moments

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It entertains. It captivates. It may even provoke hysterical laughter. But it also kinda makes you want to gouge out your eyes with a carving fork so you don’t have to watch another second of it. This (mostly new) phenomenon is called Awkward TV, and we’re here to celebrate outstanding achievement in the genre. You’ll find no accidental train wrecks here (e.g., no appearing on a talk show plastered or any reality shows, period), just premeditated squirm intended to make you feel uncomfortable. Here are the 17 Most Awkward Comedy Moments in TV History. (Why 17? Because it’s awkward!)

1. The Office (U.K.)
Season 2, Episode 4 (2002)

The Moment
On his first (and only) paid motivational speaking gig, a cocky David Brent (Ricky Gervais) proffers a twisted philosophical metaphor about how he’d rather be dead than have no arms and no legs, and concludes with an unsuccessful attempt to win over the bewildered crowd with an unending one-man clap line to Tina Turner’s ”Simply the Best.”

Why It’s Awkward
Gervais’ Office is the progenitor of the Modern Awkward Movement, the cringefest to which all cringefests are compared. And though Brent’s clueless humiliations may be many, the fact that this one happens among strangers, not co-workers, elevates the pain level to Hall of Fame status.

2. Seinfeld
Episode: ”The Pick” (1992)

The Moment
Jerry gets caught picking at his nose. ‘Nuff said.

Why It’s Awkward
Truth is, Seinfeld — co-created by Awkward Auteur Larry David — is all about lives lived uncomfortably. The choicest nuggets are so iconic, no description is necessary. The Funny Dance. The Eclair. Puffy Shirt. And the painful genius of Seinfeld’s awkwardness isn’t just the sometimes familiar, sometimes absurd scenarios — it’s watching Jerry and his nonreflective, socially inept pals try (vainly) to dodge the inevitable ramifications. This classic busted! moment — complete with Jerry’s memorably lame protest (”It was a scratch!”) — is our pick-of-the-litter choice.

3. Da Ali G Show
Episode: ”Peace” (2004)

The Moment
As alter ego Borat — that cluelessly offensive TV journalist from Kazakhstan — Sacha Baron Cohen entertains the patrons of a Tucson, Ariz., country & western bar by performing a catchy little ditty with such lyrics as ”Throw the Jew down the well/So my country can be free/You must grab him by his horns/Then we have a big party.” Apparently not in on the joke (Borat is fake; Baron Cohen is Jewish), the crowd starts cheerfully clapping to the beat and singing along.

Why It’s Awkward
You’d expect Borat to be met with stunned silence or, more appropriately, boos. Nope. The audience delights in accompanying him on one of the most offensive songs ever written.

4. Fridays
Episode: Feb. 20, 1981

The Moment
Midway through a pot-smoking sketch on ABC’s Saturday Night Live knockoff, guest host Andy Kaufman bails out, saying, ”I feel stupid,” and then sits in jittery silence. Trapped, his three stranded acting partners (including Michael Richards) veer from confusion to anger, until Kaufman pours a glass of water on Richards, producer Jack Burns throws punches, and the show abruptly cuts to commercial.

Why It’s Awkward
The other actors and Burns were in on the joke, but viewers never knew the whole thing was a gag: All they saw was Kaufman (an awkward-comedy pioneer) earning the palpable hatred of his costars. Ha?

5. The Office
Episode: ”Diversity Day” (2005)

The Moment
When Kevin’s (Brian Baumgartner) monotone reenactment of Chris Rock’s ”N — -as vs. Black People” riff at a Dunder Mifflin sensitivity training seminar makes Michael (Steve Carell) twitchy — he’s ruining the bit! — the wannabe funnyman finally interrupts and unleashes his Rock homage, a screechy, jerky, minstrel-show-worthy performance. ”Whatchoowant, a cookie?” Crickets.

Why It’s Awkward
Rule No. 1 in the Handbook for the Reconstructed White American: Never mimic anyone who isn’t white. But the awkwardness is also painfully universal — it’s the well-meaning joke that goes egregiously awry. Good intentions plus crappy execution — a formula The Office works so ingeniously — is the mathematical framework of almost all awkward comedy.

6. Curb Your Enthusiasm
Episode: ”The Survivor” (2004)

The Moment
At an anniversary dinner for Larry (Larry David) and Cheryl (Cheryl Hines), Survivor’s Colby Donaldson is dragged into a game of who-had-it-tougher with a different kind of survivor — a Holocaust one. (Colby: ”We had very little rations. No snacks!”) The absurd one-upmanship culminates with the two men violently shouting ” I’m a survivor!” at each other — and gravy flying into Larry’s face.

Why It’s Awkward
Curb isn’t afraid to mine humor from the taboo, and if a reality-show contestant comparing his struggles to the pain of someone nearly killed in a horrific genocide doesn’t make you wince, you’re a bad person.

7. Freaks and Geeks
Episode: ”Girlfriends and Boyfriends” (2000)

The Moment
Dim-witted high schooler Nick (Jason Segel) lures girlfriend Lindsay (Linda Cardellini) into his basement lair, pops in an eight-track, and begins serenading her with Styx’s ”Lady.” Lindsay’s reaction quickly turns from delighted to disturbed as Nick gets increasingly — and embarrassingly — animated. ”You wanna make out or something?” she finally asks in an attempt to break the tension. ”No,” he replies. ”All guys wanna make out. But I just want to hold you.”

Why It’s Awkward
Because it represents teenagedom at it’s most uncomfortable and relatable: that moment when you try to be all smooth but don’t really know how and come off creepy instead.

8. The Larry Sanders Show
Episode: ”Hank’s Contract” (1992)

The Moment
As the pompous-doofus sidekick to HBO’s great fictional talk-show host, Sanders (Garry Shandling), Jeffrey Tambor’s Hank Kingsley wants a raise. Hank doesn’t help his case by reminding Larry about the time he ”chipped a tooth on the bathroom urinal” and asking why Larry found that funny. ”It was a back tooth,” murmurs Larry.

Why It’s Awkward
Shandling’s confrontation-phobic Larry is squirmily uncomfortable discussing money, preferring to leave that to his producer Artie (Rip Torn), whom he puts on speakerphone without Hank’s knowledge. But Artie coughs, revealing that he’s eavesdropping, leaving all three unnerved.

9. Arrested Development
Episode: ”The Righteous Brothers” (2005)

The Moment
After two years of foreplay, teenagers George Michael (Michael Cera) and Maeby (Alia Shawkat) kiss. The scene would be tender and adorable if they weren’t first cousins.

Why It’s Awkward
If we have to spell it out for you, remove your brother’s lips from your neck and reread the previous sentence. Incest spawned some of the show’s strongest episodes, including ”Motherboy XXX,” an Oedipal gala for mothers and sons, and ”Afternoon Delight,” which summons the kind of discomfort that can only be felt by watching an uncle and a niece perform the Starland Vocal Band song. (”Thinkin’ of you’s workin’ up my appetite/Looking forward to a little afternoon delight.”) Hee hee hee… Sorry — we mean ewwww.

10. Late Night With David Letterman
Episode: Nov. 16, 1983

The Moment
Larry ”Bud” Melman (the late Calvert DeForest) is dispatched by Dave to conduct interviews and offer hot towels to tourists at the Port Authority Bus Terminal.

Why It’s Awkward
For one thing, he’s impossible to hear, because amateur Melman keeps pointing his handheld microphone at the bus passengers while he’s talking. (”It’s like a ventriloquist-in-training,” remarks Letterman to the howling studio audience.) And visitors from Virginia and Maryland are politely puzzled and have no clue how to response to Melman’s oddball generosity.

11. The Comeback
Episode: ”Valerie Triumphs at the Upfronts” (2005)

The Moment
Valerie Cherish (Lisa Kudrow) hits a big presentation to advertisers in NYC to promote her new show, Room & Bored, and is subjected to multiple indignities. First the washed-up sitcom star is accidentally left behind on the way out to a cast dinner. Then she breaks into tears and uncharacteristic swearing off stage when the network fails to introduce her with the rest of the cast.

Why It’s Awkward
It’s here we get our first glimpse of the barrage of embarrassments (cupcake costumes, projectile vomit) coming Valerie’s way. Sure, the network does eventually call her on stage for her reality show, but that’s just the kind of cruel give-and-take that kept Valerie — and us — going for the whole season.

12. Extras
Season 2, Episode 5 (2007

The Moment
To boost his cred with critics, Andy (Ricky Gervais) takes a gay character role in an Ian McKellen play but gets cold feet when a bunch of homophobic school chums come to opening night and he has to plant one on a fellow. As a result, Andy starts ad-libbing and pushing away his puckered-up costar while stealing concerned glances at his horrified classmates.

Why It’s Awkward
It’s a classic cringe-worthy clashing of two worlds. In trying to please both camps, Andy ends up alienating everyone. We see it happening and yet are powerless to stop it.

13. Sex and the City
Episode: ”Running With Scissors” (2000)

The Moment
After skulking around for weeks with married ex Big (Chris Noth), and with secret rendezvous spots growing seedier, Carrie (Sarah Jessica Parker) wants to end the affair. But just one more nooner at Big’s apartment can’t hurt, right? Too bad his wife, Natasha (Bridget Moynahan), comes home early, catches Carrie, then falls and breaks a tooth running after the little home-wrecker.

Why It’s Awkward
We’re not sure what’s more painful: Natasha’s header down the stairs, or watching her lock a cab door to try to block Carrie from accompanying her to the hospital.

14. The Tom Green Show
Season 2, Episode 5 (1999)

The Moment
The man of a thousand pranks (Tom humps moose roadkill! Paints his parents’ house plaid!) stealthily trails a pizza delivery guy and then tries to undercut him in front of his customers with another pizza and a tackle box of toppings. Even after he’s profanely told to take a hike — and one of the irritated customers kicks over the tackle box — Green keeps pushing his pie, right up until he’s chased away by the hammer-wielding customer.

Why It’s Awkward
Although you can cut the tension with a pizza wheel, Green ignores all obvious danger signs, ultimately provoking a dude to come after him with a hammer.

15. Cheers
Episode: ”The Days of Wine and Neuroses” (1991)

The Moment
On the eve of finally marrying her dream ex-millionaire, Robin Colcord (Roger Rees), Rebecca (Kirstie Alley) gets sloshed and tries to woo Sam (Ted Danson) with a serenade of ”We’ve Got Tonight.” Looking at Rebecca’s ratty bathrobe and dangling cigarette, Sam demures, ”First of all…a gentleman has rules. And second, you’re kind of repulsive right now.”

Why It’s Awkward
Alley’s Rebecca joined the show in ’87 as a humorless hard-ass, but over the years the character got more and more hopeless and hilarious. This ’91 episode was her delightfully pathetic (or vice versa) low point.

16. Dog Bites Man
Episode: ”Gas Prices” (2006)

The Moment
This short-lived Comedy Central series from Ali G producer Dan Mazer featured a local news team preying on oblivious participants. Here, nerdy assistant Marty (A.D. Miles) moonlights as a horrific comedian, stunning a real audience into silence with an endless string of lame sound effects and botched catchphrases. (”I’m sorry, I didn’t get the memo!”)

Why It’s Awkward
As if the brutal bombing wasn’t excruciating enough, backstage he bats away a talent agent’s frank criticism, convinced that making more sound effects will win her over.

17. Wonder Showzen
Episode: ”Patience” (2005)

The Moment
Proving that even a cuddly puppet can make people’s heads explode if he’s annoying enough, fuzzy blue Clarence confuses and enrages his interviewees by asking them to tell kids ”it’s important to be patient” and then interrupts until his subjects lose theirs. Kermit never had someone take a roundhouse kick at him or scream for the cops.

Why It’s Awkward
Even more unnerving than watching a puppet provoke violent outbursts in the name of teaching children? Those nervous subjects who politely endure his endless provocations: If Clarence told them to kill ”for the kids,” they just might.

Written by Jennifer Armstrong, Henry Goldblatt, Jeff Jensen, Dalton Ross, Dan Snierson, Ken Tucker, Alynda Wheat, Josh Wolk