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 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; 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.; Don't even try to watch any of his shows if you are even slightly sensitive to this kind of thing.
The My Little Pony: Friendship Is Magic fic "Naked Singularity". It's 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 indecipherable. Then she reads it to a coffee shop with Celestia, Twilight's parents, a class of schoolchildren...
Bridesmaids: when the main character is getting the attention of a cop who doesn't want to acknowledge her, among numerous other examples.
Frances Ha is fairly low-key Cringe Comedy, but much of the film's humour nevertheless consists of this. The main character enacts her eccentricities in inappropriate situations, e.g. by trying to inaugurate someone as a new BFF by one-sidedly play-fighting with her. In general, Frances' failure to fit in with the adult world is a source of much of the film's comedy.
Charlie Runkle's role on Californication. Examples include his masturbation at work habit becoming known through a viral video and was taken to a new low (or high perhaps) with his season 6 plot about pretending to be gay to sign a client.
The IT Crowd:One episode has Roy go underneath a woman's desk to plug in her computer. She comes back to sit at her desk and he ends up trapped since he couldn't possibly get out without looking like a pervert.
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 Tom Green Show; 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. Examples including airbrushing two very Not Safe for Work lesbians on the hood of his dad's car, and hiding an elaborate contraption under his lab coat while claiming that he was converting grape juice to pee...on a public bench.
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. For whatever reason, about half of them are Clark's painfully awkward interactions with women, and half of those are with Chloe.
Most iterations of The Office feature this type of humor. Examples from the most famous versions of the series include:
The Office (US): Ten years prior to the series, Michael Scott promised a group of inner-city youths that he would pay for their college educations if they would make the necessary grades. Ten years later, Michael must go to these inner-city youths and tell them he's not able to pay for their educations. But before he can do that, they sing a song about how he will make their dreams come true.
The Michael J Fox Show, though possibly unintentionally. One notable example is Mike's neighbor saying that he "doesn't know what it's like to struggle" as Mike is in the background, struggling to open a jar that his 10 year old opens with ease.
Girls has never been a series to shy away from cringe humor, but Marnie's cover of Kanye West's "Stronger" is one of the most uncomfortable points of comedy in the series. All the more so due to the fact that she's completely unaware of what a complete ass she's made of herself.
The Inbetweeners makes you cringe very often. Even in the first episode, where Will doesn't have ID in a pub surrounded by nearly his whole school year. He goes on a rant about how everyone in the pub is under-aged, and gets them all kicked out.
Parks and Recreation is usually upbeat, but the moment where Leslie (along with several members of her team) walks out onto an ice skating rink, only to find her red carpet isn't long enough is this. It also involves a three legged dog that starts to pee on Ron, everyone slipping and falling, and then when she gets to the stage, it has no stairs. As this happens, the song "Get on your feet" by Gloria Estefan starts and repeats several times.
Extras is particularly brutal with this. When one woman on the set brings her sister (who has Cerebal Palsy) to the set, Andy makes a joke that she looks drunk and "mental", right in front of her sister. He manages to save this one, though. There are other scenes that are much, much worse.
Friends dabbled in this from time to time, usually at Ross's expense.
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.
Daxflame's videos tend to evoke cringing in viewers through his recounts of awkward social interactions and his total obliviousness to his own social insensitivities.
Cringe Channel, to be found here, aggregates unintentional cringe comedy from all corners of the internet. Even though this is a definite case of laughing at the given subject in almost all instances, certain postings and many commentators take a more aggressive and transparently mean-spirited approach towards their subjects.
Know Your Meme has a meme and image gallery called "Cringeworthy" that collected various instances of embarrassing and stupid things, but the addition of new images was locked after people started using it for Complaining About Shows You Don't Like (by adding images that were only the logo of things they disliked) and spamming the gallery with several parodies of other images (of note are the many, many parodies of a poor drawing of The Rake saying "Time to killed people!" and of some SonicOriginal Characters called Jake and Maribelle. While the original images were cringeworthy, the parodies were not)
Game Grumps can tend delve into this when talking about Dan's past, especially dating.
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.
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 Bros. utilizes this several times a season, mostly with the main character Rusty Venture though other characters are also occasionally guilty of this trope.
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. 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."
The most clear cut example is probably the episode "Maud Pie", where Pinkie's sister visits town and the cast has a horrendously difficult time attempting to get to know her better due to her extreme stoicism.
Equestria Games has the scene where Spike interrupts a medal ceremony to insist on singing the gold medal-winner's anthem. Only after Shining Armor announces this to the crowd does Spike realize that Cloudsdale (not Ponyville) won the gold for that particular event. Spike doesn't know any of the words to Cloudsdale's anthem. As he ad-libs, the camera cuts multiple times to the audience, who are just as embarrassed as Spike is. One unicorn even yanks his top hat down to cover his entire head.
A Friend In Deed is this to people who have had to deal with an annoying hanger-on, or realized too late that they were that hanger-on — or both. Same with Party Of One, with an added dose of social anxiety. Most Pinkie Pie episodes have at least a little of this.
The Amazing World of Gumball: In "The Gi", Gumball and Darwin wear their karate uniforms to school and get soundly mocked by their peers (the duo's nickname is the "Karate Weiners") when they start doing low-grade karate in front of everyone, much to their obliviousness. Nicole is the "cringe-ee" here, as she keeps trying to discourage them without outright saying they're making fools of themselves. At the end Gumball gets a hard dose of reality when he realizes what's really going on, which is a little sad (although the episode ends on a Crowning Moment of Heartwarming right afterwards).
The main point of all those "Tell Your Most Embarrassing Moment" sections in every teenage girl's magazine ever.