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.
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 awkward 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 C.K. 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.
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.
Charlie Runkle's role on Californication. Examples include his masturbation at work habit becoming known through a viral video and was recently taken to a new low (or high perhaps) with his season 6 plot about pretending to be gay to sign a client.
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.
Malcolm in the Middle. One famous example is Malcolm flipping out in front of a bunch of his friends and the girl he likes at his mother who was the 'chaperone' for them at a bowling alley, because he sucks at the game. He walks down the lane to the pins, throws it and still misses.
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 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 HBOSitcom.
The Tom Green Show was one of the more grotesque examples of this. Blending Black Comedy and Surreal 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.
Saturday Night Live, especially from the 1990s to now (the '70s and '80s episodes often drift in and out of cringe comedy). Some examples include: the "Canteen Boy Gets Molested" sketch, a lot of the sketches based on real world awkward situations, and, of course, this.
Impractical Jokers has a lot of this. Half of the show is the guys laughing at what they've come up with, and their victim's reaction to what he has to do, which are mostly funny. When they are actually going through with it, however, awkwardness galore.
For a supposedly serious show, Smallville indulges in this. A lot. For whatever reason, about half of them are Clark's painfully awkward interactions with women, and half of those are with Chloe.
The Opie & Anthony Show: Everything from stomping on a homeless man's cake to playing laugh tracks behind a caller mentioning the death of a relative. They even embraced the term "Cringe Radio" for their type of show.
Mega 64 has this in most of the public video game imitations.
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 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."
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. Two of the pranks weren't pranks so much as they were humorous physical assaults. One involved punching LG in the belly and pushing him onto the floor. The other involved lacing his food with burning-hot chemicals and causing him to fall out of a window. And it's hilarious.
Peppermint Butler: He's eating the dirt! Spice it now!
The outrageously funny scene where Principal Skinner treats Superintendent Chalmers to dinner in The Simpsons episode "22 Short Films About Springfield".
The Flintstones did a lot of this as Getting Crap Past the Radar. One incident involves Wilma being pregnant with Pebbles and Fred has to be certain he can get her to the hospital in time, so he enlists Barney to help him. She has contractions so they rush her to the hospital, more-or-less in a panic. They arrive at the hospital, Barney rushes Wilma through the revolving door so fast it spins Fred out of the building, and across the street through the revolving door of another building, which Fred does not realize isn't the hospital, but a hotel. Hilarity Ensues when Fred, wanting to know where in the hospital Wilma is, innocently says to the desk clerk, "I'm looking for my wife. She just came in here with my best friend."
This may be the main point of all those "Tell Your Most Embarrassing Moment" sections in every teenage girl's magazine ever.
To explain, it is about Twilight writing a pornographic story involving expys of her and a few of her friends. A lot of the humor comes from the science allusions and technobabble that makes the story almost indecipherable. And then she reads it to a coffee shop with Celestia, Twilight's parents, a class of schoolchildren...
At a campaign event in 2008, American Vice-Presidential candidate Joe Biden asked State Senator Chuck Graham to stand up and greet the crowd. Graham was in a wheelchair.
U.S. Senator Marco Rubio's awkward water-drinking during his rebuttal to President Obama's 2013 State of the Union speech.