Cringe Comedy

A big trend in modern TV comedy: shows where the humour mostly comes from placing characters in the most embarrassing situations possible, or having them say the most awkward or offensive thing possible at all times. Often uses documentary feel to heighten the naturalism and increase the cringe, or has actors in character interacting with an unsuspecting public. Comedy you have to watch through the gaps between your fingers.

Often this is mollified by the characters being oblivious to the embarrassment they should be feeling. Sometimes though, all the characters are acutely aware of their humiliation, which can make it so much worse. Or worse yet, there's a single Audience Surrogate character who realizes how humiliated everyone should be feeling, while everyone else remains oblivious.

Some shows specialize in this sort of humor. Others include a scene of it here or there, largely avoiding it. Still others make this sort of thing a sort of Running Gag, as with taking a character who can't act and requiring them to play a part for the good of the team—repeatedly.

German, the language that brought you "Schadenfreude", has recently developed the term "Fremdschämen" ("vicarious shame/embarrassment") to cover this phenomenon.

See also Crosses the Line Twice, where the same basic material is used, but more to make people laugh than to make them uncomfortable.

Examples of Cringe Comedy include:

Anime and Manga

School Rumble. Especially after Harima became the main character.
It's Not My Fault I'm Not Popular!
Episodes 7 and 8 of Persona 4: The Animation are built on this.

Film

Borat
Bridesmaids: the bridesmaid's dress fitting, the plane trip to the Las Vegas bachelorette party, the bridal shower. And when the main character is "helping" customers at work, and also when she's getting the attention of a cop who doesn't want to acknowledge her.
Bruno
The "Hair Gel" scene from There's Something About Mary.
Numerous Seth Rogen flicks.
Meet the Parents, the dinner scene. Perhaps they were attempting to replicate the success of There's Something About Mary.
Along Came Polly
Many Christopher Guest movies tend to fall into this at times.
Napoleon Dynamite. Fortunately (or not) the main characters seem to be incapable of feeling embarrassed.
The original 1972 version of The Heartbreak Kid was a groundbreaker for this. Going back even earlier, The Graduate has quite a bit for Dustin Hoffman's character of Benjamin.
Johnny English
The 40-Year-Old Virgin.
Death at a Funeral has several choice scenes of this. Alan Tudyk at a funeral + acid - clothing = cringe comedy gold.
Forgetting Sarah Marshall
Harry's post-laxative scene in Dumb and Dumber is both this and Refuge in Vulgarity.
The pie scene in American Pie.
In the Loop
Martin Scorsese's The King of Comedy has a fair amount of this.
Dan in Real Life
The films of Agnes Jaoui and Jean-Pierre Bacri. Terribly believable situations and dialogue too.
The Bridget Jones films; even more so than the original newspaper columns.

Literature

The Bridget Jones newspaper columns (see above for the films) and subsequent book compilations.

Live-Action TV

Curb Your Enthusiasm
I'm Alan Partridge
Peep Show
The Office
Extras
Da Ali G Show
The celebrity interviews on Brass Eye.
Colin's Sandwich is an earlier example, where the embarrassment came partly from Colin's horrible bad luck and partly from his reactions to it which invariably made things worse.
Fawlty Towers
Mr. Bean, both the series and the movies. Rowan Atkinson often uses this trope.
Freaks and Geeks has a goodly amount of this. As does Undeclared. And, well, everything else Judd Apatow has done.
Coupling, especially storylines involving either Jeff or Jane.
The Inbetweeners is this for a new generation, with the added bonus that, since it's set in the Sixth Form, a LOT of the viewers have been there and can relate.
The Worst Week of My Life
The IT Crowd has these scenes in droves.
The Daily Show correspondant interviews, as well as many The Colbert Report interviews
Seinfeld, especially George Costanza (even more for what he does than what happens to him)
About half the humor in Monk comes from this.
Short-lived Seth MacFarlane series The Winner had so much of this.
The Thick of It
On Mister Ed, Wilbur Post lives this trope.
Malcolm in the Middle
A episode of House had Chase making a Your Mom joke to Foreman as a witty comeback. Some fans couldn't even watch the ensuing train wreck.
The Increasingly Poor Decisions of Todd Margaret
The Stargate Atlantis episode "Duet" has Rodney McKay on a dinner date. Doesn't sound so bad, except: a) Rodney is naturally awkward in social situations, especially when there is a woman involved; and b) Rodney has a female consciousness in his head at this point, giving him dating advice in a voice only he can hear.
The Comeback, Lisa Kudrow's short-lived HBO Sitcom.
The Ted and Ralph sketches from The Fast Show. Ralph is the socially awkward upper-class proprietor of an English estate, while Ted is an elderly Irish man who tends to the estate's gardens. Ralph is in love with Ted. Hilarity Ensues.
- "I'll get me coat."
While not necessarily a comedy, Twin Peaks sometimes dives into this during the show's more awkward moments.
An episode of Community when Jack Black tries to join the study group. His usual antics lend this to his scenes.
Frasier had this in nearly every episode.
New Girl uses this trope a few times in the Pilot Episode.
Trollied has a bit of this, most notably Julie's job interview.
An iron stomach is required to get through an episode of Tim and Eric Awesome Show, Great Job! without looking away in embarrassment.
The Tom Green Show was one of the more grotesque examples of this. Blending shock comedy and surrealist humor, Tom would go out of his way to create the most embarrassing, and often disturbing, situations possible for his sidekick Glenn Humplik, random people on the street, audience members, and even his own parents.
A fair share of the humour in The Big Bang Theory is this.

Music

Flight of the Conchords. The song "Jenny" is probably the most awkward conversation ever set to music.

Recorded and Stand Up Comedy

Ben Stiller is married to this trope; look at every role he's played dating back to his own show, both as host and in every one of his skits.
In the late '60s and the '70s, German comedian Loriot basically created his entire career completely on sketches about uptight middle class people who get into awkward situations and make everything worse by being completely oblivious about it. It becomes much more bearable by the fact, that usually nobody seems to be aware that the situations should be akward and everyone continues as if everything would be fine. As a parody of how people of those decades refused to allow any loss of face to the point where it got painful, his show got massively popular. As an example, "German for Foreigners", or known to most people as "This is my briefcase", or "People on a plane".
Louis CK is made of this. Don't even try to watch any of his shows if you are even slightly sensitive to this kind of thing. On second thought go ahead. There can not be anyone who can finish an episode without pausing at least 5 times. At least not while sober.
The Dead Alewives Dungeons and Dragons sketch from the Take Down the Grand Master CD is pretty darn cringe-y.

Web Comics

Asperchu becomes this once you realize that CWC becomes a rampaging self-parody when he's turned into a fictional drawing, with literally no exaggeration whatsoever.

Web Original

Mega 64 has this in most of the public video game imitations.
The Guild
While That Guy With The Glasses doesn't usually have this, The Nostalgia Chick's first "Thanks For The Feedback"—where she goes on a date with the Critic—is horrifying in awkwardness.

Western Animation

The Life and Times of Tim
Older South Park episodes, and some newer ones rely on this heavily. Lampshaded in "Funnybot", where the title character even uses "Awkward!" as his catchphrase. The boys have to stop him from telling the "Last Joke Ever," in which he destroys the entire human race becaues it's the most awkward thing possible. Appropriately enough, Funnybot was designed by the gallows-humor-obsessed Germans.
The Cleveland Show
The Venture Brothers utilizes this several times a season, mostly with the main character Rusty Venture though other characters are also occasionally guilty of this trope.
Family Guy, though whether or not it's funny or just plain offensive is based entirely around one's point of view. A good example is the Cutaway Gag "Horton Hears Domestic Violence In The Next Apartment And Doesn't Call 911."
SpongeBob SquarePants in its later seasons.
Most of Don Hertzfeldt's works are dark comedies, or surreal dramedies. One film, however, is "Lily and Jim", telling the story of a blind date from the perspective of both people. It is complete Cringe Comedy.
The Ren and Stimpy Show often goes into this territory.
Adventure Time often goes here- most notably in Too Young, with Finn and Princess Bubblegum's more painful (literally causing physical pain) ways of pranking Lemongrab.
The outrageously funny scene where Principal Skinner treats Superintendent Chalmers to dinner in The Simpsons episode "22 Short Films About Springfield".

Other

This may be the main point of all those "Tell Your Most Embarrassing Moment" sections in every teenage girl's magazine ever.
YMMV may vary on whether this is actually the case (and don't tell us eother way), but it was referenced in relation to Sarah Palin 's Katie Couric interview in the book Going Rogue.