Face of a Thug
"Maybe then you could buy yourself a face that doesn't scare small children."
—Yami to Kaiba, Yu-Gi-Oh!: The Abridged Series
This is where a character is shown to have a very scary, thuggish face—mostly for comedic purposes. The expression will often include a Kubrick Stare, where the face tilts down but the eyes look up. The face of a thug is so scary that normal people are shown to be easily scared off just by looking at them, and can make even tough brutes feel uneasy.
The catch here is that that the character with the face of a Delinquent is anything but. Some of them are genuinely nice, even exceptionally so; others are actually cowards surviving solely based on their looks. Generally, though, they are normal people who would rather just have a normal life.
Things aren't that easy, though. Since everyone assumes them to be a Badass of the highest degree, other people will either avoid them for fear of getting involved, or try to rope them into fights far beyond their actual ability. Their actions will usually revolve around trying to make normal people acknowledge their true self, while avoiding that the thugs around them learn the truth about the same.
This can often result in a delinquent who doesn't act like a delinquent. Such a character may even have actual skill at fighting and street survival, not because they choose to live that way, but because they had that kind of life forced on them. They had to pick up those skills to survive.
Please note that it doesn't necessarily mean "ugly", even though most of the examples below are. It's more about looking threatening than actually looking bad, and it's possible to look both handsome and fearsome.
There is a real life 'condition' called resting bitch face (especially on the internet). Someone with this, when at ease, has a face that falsely conveys that they are "angry, annoyed, irritated, or contemptuous". This is as prevalent in males as it is in females. 
- When in public, the protagonist of Mononoke Sharing sometimes wears fake glasses to hide her scary eyes.
- This trope is Kitano from Angel Densetsu. In fact, the whole plot is driven and catapulted by how he looks like a horrible thug that does drugs and kills people with impunity, which causes everyone to fear and respect him. Of course, all of that is false, and he's the nicest person on earth. His bizarre behavior doesn't improve his image either.
- Narumi of Karakuri Circus, amongst others.
- Seiji from Midori no Hibi has a face of a thug. It's why he constantly has a stream of bullies challenging him, which led to how he became so good at fighting. However, underneath, he's actually a Jerk with a Heart of Gold who wants to be loved.
- Oga from the manga Beelzebub, who is known as the "strongest juvenile delinquent." He attempts to scare away a baby who has grown attached to him by making his face even scarier than it already is. However, it backfires, since the baby is actually Satan's son, and therefore actually likes incredibly scary faces.
- In Oga's case, he actually is a delinquent instead of just looking like one. Although he is arguably a much nicer person in comparison to other delinquents around him.
- Tojo is a more straight example. He is very tall and muscular on top of having a scary face, and even though he likes to fight, he is a genuinely Nice Guy who also has a weakness for cute things.
- To be honest, since about 99% of the cast are Delinquents, most of them count for this trope.
- Sig Curtis from Fullmetal Alchemist is an enormous bear of a man, and a butcher by trade. He often frightens small children with his size, looks, and sharp implements. Ironically, while he is usually a kind, gentle man, his much less imposing wife is an easily angered firebrand of a woman (though never to him).
- Alphonse Elric is a sweet, gentle 14-year old boy whose voice never broke... whose soul inhabits a towering suit of spiky, badass armor. Frequently mistaken as the Fullmetal Alchemist; only in Super-Deformed do his true colors show. Observe.
- Ling Yao, a mildly suspicious but otherwise amiable guy who values his comrades and is also one of many heirs to the Xing throne admits to knowing that he doesn't have the friendliest looking eyes when Ed points out he wouldn't trust Ling's face. Ling deliberately keeps his Eyes Always Shut for the most part because of this.
- Sousuke Sagara from Full Metal Panic! is shown to have such an intense, intimidatingly scary face that it scares off anyone who approaches him or Kaname. It happens mostly for comedic effect, and he's shown to actually be very attractive when he lightens up a bit.
- On the other hand, Sousuke is extremely violent by nature (due to being raised by resistance fighters and all that). He's just highly professional about it rather than being a thug.
- Very oddly, although Sousuke wears a stern expression and has prominent scars on his face, he's actually quite Bishonen when you add it all up. In some cases Even the Guys Want Him.
- Sakaki Shio from Kenichi: The Mightiest Disciple. He is a huge muscular guy with a scarred face and looks very scary and violent. While that's partially true because he is a Dou fighter (one who fuels his martial arts by rage and aggression) he is the Master who cares and worries about Kenichi the most, going out of his way to protect him.
- Kasanoda (AKA Bossa Nova AKA Casanova) from Ouran High School Host Club. He's actually an incredibly gentle soul, who loves cute things. The only problem is that he just scares the heck out of everyone because of his thuggish face. The Host Club try all sorts of ways to "soften" his appearance, but all their efforts seem to only make him seem more unnerving and scary. Eventually, his crush on Bifauxnen Haruhi leads him to be Mistaken for Gay by his Yakuza underlings, and the Host Club's sizeable Yaoi Fangirl clientèle, who start seeing him as Troubled but Cute.
- This guy terrified his father (boss of the biggest Yakuza gang in the city) when he was five, his face is so terrifying. He was just born that way.
- Sunako from The Wallflower has a face that isn't so much like a thug, but a ghost. It scares pretty much everyone to death. She's revealed in rare instances to clean up nicely.
- Ichigo from Bleach has the looks and face of a delinquent. Apparently, his natural-colored orange hair doesn't help convince anyone otherwise (since they think it's dyed). However, it's later shown that he actually gets very good grades in class, if only because he'd rather stay home and study instead of going out and getting drawn into fights.
- Don't forget Chad, who looks rather intimidating (and is physically bigger/more muscular than most people) but is in fact much more of a Gentle Giant. Of course, Chad once used to be a thug when he was younger, but in the first arc, it was shown how he never fights unless it is to protect someone/something, even if he is struck first.
- Randoh from Pretty Face, before the whole mess with the surgery that made him look like his crush. He's a Jerk with a Heart of Gold delinquent, and certainly looked scary.
- Leo Aoi from the manga BeastMaster, who looks like he's always giving everyone the death glare. When introduced to the class as the new transfer student, everyone is shown shaking in fear, and even the teacher is shown to say while sweating, "Everyone, please be kind to him. Don't be afraid of him." It turns out that he was raised in a wild jungle, but is actually very gentle and kind. This doesn't stop other delinquents from thinking he's a super violent thug that wants to challenge them.
- Ryuuji from Toradora!. It's genetic apparently. He's really quite kind, and enjoys doing housework (especially cleaning). His looks and personality are made to contrast Taiga, who looks cute, but is actually ferociously violent.
- Chiba Seiya from Yankee Kun to Megane Chan is really a timid, studious nerd, but has the face of a delinquent thug. Naturally this leads to numerous unwanted confrontations.
- Sakaki from Azumanga Daioh. She's tall and imposing, so everyone assumes she's a juvenile delinquent. In reality, she loves everything cute and cuddly.
- Interestingly, one episode had a "dress-up race" and Sakaki dressed like a stereotypical male delinquent.
- Principal Enzo from Crayon Shin-chan, whose face is so scary and thuggish, it scares not only the children, but also the teachers. It's to the point where the children take to calling him "Kumichou" (which means "Godfather"). However, he has a tender heart, and is shown to actually be a very nice person.
- Parodied and subverted in Sayonara, Zetsubou-sensei. Mayo Mitama has creepy looking eyes, but since Dark Is Not Evil, everyone is still nice to her, thinking she fits this trope. Turns out they are all Wrong Genre Savvy and not only is she really as evil as she looks, she exploits this trope to do all the villainy she can. However, it is implied that she does all those bad thing hoping that just once, someone would call her out on it.
- Misao Zaitsu from Hatsukoi Limited. He also has a Funny Afro going for him, and looks terrifying. But he's as much of a lovelorn idiot as the rest of the cast.
- Poor, poor Sweden from Axis Powers Hetalia. His Death Glare scares the crap out of everyone, his partner Finland included... but after leaving his Viking life, he's actually one of the sweetest nation-tans.
- Harima Kenji from School Rumble.
- Keith Gandor from Baccano!! may as well be carrying a neon sign reading "I am in The Mafia. Fear me," given his appearance... Okay, so he is in the Mafia, but more of the honor-bound Noble Demon Neighborhood Friendly Gangsters variety. The Light Novels describe his face as "the face of a man who, no matter how you looked at him, didn't seem as though he did proper business."
- Usui Kenta from Karin has this problem, albeit mildly. To the people around him, his neutral face seems to be a glare.
- However, Kenta picks up on the 'kind-hearted' bit. He is quite likeable.
- His actual glare is capable of scaring off a street thug. The manga shows a glaring cobra in the background when he does this, just to drive the point home.
- Tomoka Kayahara from Muteki Kanban Musume, unless she's enjoying a meal, has a face that frightens children, small animals, adults, and Megumi.
- The main cast in Dorohedoro mostly plays it straight only when they have their masks on, and avert it by taking them off (Except Cayman of course). En even manages to be a cute little boy in a flashback (Given, an Ax Crazy Omnicidal Maniac Complete Monster Little Boy, but hey, it's EN).
- Kaidou Kaoru from Prince of Tennis, to a degree. Most of the regulars (from Seigaku and otherwise) and teachers have no problem with him, but practically every other student he meets (especially the younger ones and girls) consider him to be terrifying. In fact, on one occasion, two nasty girls from another school were planning to humiliate him after he won a match against their school—when he turned around to see what they wanted, they freaked out so badly that one of them smashed her can of soda onto her own head.
- Humorously, old people (especially elderly couples) tend to find him very nice and consider him a 'good boy', rarely even noticing what he looks like. This usually makes him blush.
- Zoro from One Piece, despite being a generally good guy and a Friend to All Children, is often accused of having a scary face (and his Slasher Smile is enough to freak out even the viewers).
- Captain T-Bone of the Marines is an even better example. He looks like a zombie or ghoul but he is one of the most compassionate and caring people in the whole series, ripping his own mantle to pieces just to provide bandages for his wounded men.
- The cut wasn't even that bad...
- Simon from Durarara!! is a friendly, peaceful and intelligent sushi tout. He is also a seven-foot-tall Scary Black Man that tends to scare off passers-by with his mere presence. Interestingly enough, the really dangerous guy in the show, Shizuo, is a slim blond Bishonen, and so unfortunate people sometimes underestimate him and are crushed by flying vending machines.
- Sasayama of Kurosagi Corpse Delivery Service is bald with a nasty-looking scar on his head, and has only one working leg. These traits, coupled with his style of dress, makes the protagonists initially think he is a Yakuza. However, he's actually a former cop and currently works in social services, and is a good guy. To a lesser extent, there's Numata, who looks like a tough guy, always wearing leather jackets and sunglasses at all times. However, he also listens to J-pop groups, and the reason for wearing his Cool Shades completely subverts the thuggish image he's a highly emotional guy, and they hide tears.
- From Katekyo Hitman Reborn, we have Lanchia, who despite being quite scary looking, is apparently a Friend to All Children. They literally like to be all over him. Though he acts like he doesn't notice.
- Rascal from Akazukin Chacha.
- Hedoro from Gintama is an almost unfathomably nice guy who runs a flower shop, respects the elderly, and literally won't hurt a fly. Unfortunately for him, he's an alien who looks like a Tokusatsu Monster of the Week combined with Satan.
- Makoto/Sailor Jupiter from Sailor Moon, sorta. While she did get into a lot of fights at her old school (and still got into some after transferring, even before becoming Sailor Jupiter), she's a nice girl who loves to cook and is great at cleaning.
- Sawako Kuronuma, the protagonist of Kimi ni Todoke, has frequently been mistaken for a nightmare-inducing ghost due to her appearance, particularly when she tries to smile. In reality, she's an incredibly withdrawn girl with the heart of a saint.
- Boku wa Tomodachi ga Sukunai: Kodaka Hasegawa not only has the Face of a Thug, but he's also half-English, so people think his naturally blonde hair is bleached, Delinquent-style, since he otherwise has Japanese features. As a result he has no real friends and people are constantly picking fights with him.
- Reina's dad in Yandere Kanojo scares pretty much everybody away because of this trope, along with not being very sociable...though really he's a Shrinking Violet in the extreme and couldn't harm a fly. On the bright side, he met his wife, an actual thug, because she thought he looked like a total badass. She was wrong, but fell head over heels in love with him anyway and they ended up Happily Married.
- Hilariously used in an early Detective Conan case. Ran catches a huge and angry-looking man with Cool Shades spying on the Mouri Detective Agency, and he refuses to take off his glasses even after it's seen he is actually a fellow detective. The moment the glasses come off...
- Kenji Ban from Heartcatch Pretty Cure. While he has a really intense face and can give Death Glares that send even the most hardened of Delinquents running, he's really a just a sweet guy who loves drawing Shojo manga.
- Kai Shiden of Mobile Suit Gundam has mismatched eyes, a perpetual smirk, and a crooked nose. Personality wise he can be an abrasive Jerkass, but he's also an extremely brave and reliable (if at times difficult to get along with) soldier.
- The entire Sanada North Perfectual High School's Student Council in Daily Lives of High School Boys is this, save for the Student Council President who is traditionally Bishonen.
- Slam Dunk: Sakuragi is considered scary, but that's mainly because of his bright red hair. Miyagi's delinquent aura seems to come 100% from his face, however.
- Woo-Soo Choi, of Quantum Mistake is a studious boy who has swapped bodies with Kang Too-Jee, a delinquent who spent most of his time getting into fights. Woo-Soo Choi, relying on Kang Too-Jee's reflexes, is capable of putting up a fight, but most of the time, just wants to talk it out with the other guy. (This pretty much never works.)
- Geralt from The Witcher is described like this in the books. He somehow manages to get all the girls anyway. On the other hand, not too hard to believe.
- Lucas Davenport from John Sandford's Prey novels has a scar across his face from a rogue fish hook accident and, later, a tracheotamy scar on his neck. While being a well-known cop and the main character of a long-running detective novel series, pretty much everyone agrees that he looks like a thug or tough guy. Of course, that often works to his personal advantage.
- Mildmay the Fox, from Doctrine of Labyrinths by Sarah Monette. He is a former assassin, but he's not nearly as thuggish as most people assume.
- Gonko of The Pilo Family Circus has a face that "looks to have been used as sandpaper and soaked in whiskey." He's actually a clown.
- Doomsday Book has Father Roche.
- In The Illiad and The Odyssey, Several people refer to Odysseus himself as having "the face of a brute," and recount their surprise when he turned out to be a Genius Bruiser Guile Hero.
- An episode of My Name Is Earl dealt with this trope.
- Gentaro Kisaragi, the protagonist of Kamen Rider Fourze, dresses as a Delinquent with slicked-back hair. However, he's actually an affable goof who quite literally wants to be Friend to All Living Things (who can still kick ass if need be).
- The Monster of the Week in the Supernatural episode "Yellow Fever" is the ghost of a man who was murdered as a result of this trope.
- The Diamond Arm (an old Soviet comedy directed by Leonid Gaidai) has the protagonist, when he was slightly paranoid about bandits, at night runs into this guy. A huge chap in leather, twirling a skull-shaped key charm, who asks for a smoke (pretty common in USSR, but also stereotypical thug's approach) in grim or slightly threatening tone. He is completely harmless and doesn't even move, other than twirling his key charm.
- Gonzales from Fire Emblem 6, nice guy overall, looks like this
- Garret would qualify as well 
- Persona 4's Kanji Tatsumi, the tough guy who can take down a biker gang with his bare hands, is often mistaken for being in a gang, and... likes to sew. And is incredibly good at it.
- Takeharu Kirijo, Mitsuru's father, from Persona 3 would also count. When he first appears, he's described as "scary-looking", but he really cares for his daughter and feels guilty that she inherited his mistakes.
- How can we forget Shinjiro Aragaki from Persona 3, a seriously intimidating fellow who can easily headbutt his enemies into submission, he is also a great cook, cares about the Team Pet a lot, buying food for him with his own money and asks other team members to take care of their bodies, eat properly and so on.
- While not overly thuggish, Miss Viola Cadaverini from Phoenix Wright looks creepy as Hell, but discounting her relationship with Furio Tigre she's not that bad.
- Will Powers is a Gentle Giant with a face that scares small children. Kind of a handicap for an actor in children's shows, so he takes roles that involve wearing masks.
- From the fourth game, Wocky Kitaki's father. He used to be the head of the local Yakuza, and has an extremely intimidating face...but by the end of the case, it's shown that he's a loving father who brought the family out of the mob business so that his children, especially Wocky, wouldn't have to put their lives in danger.
- Detective Badd is an imposing, gruff figure, but he's practically a second father figure to Kay. He gives her Swiss Rolls and distracts her with 'important detective assistance' to keep her mind off her father's death.
- Hayden from Harvest Moon: Tree of Tranquility/Animal Parade. It's a bit of an Informed Ability, because he looks as cute and Chibi as everyone else, but according to characters in-game, his bearded face and Big Ol' Eyebrows are so offputting they scare children. Which is sad, because Hayden is a domestic, softhearted bartender who's almost universally liked in the town.
- And then there's Ganon in Sunshine Islands. He's got a pretty creepy/ugly face and walks/looks kinda like a gorilla, but once you befriend him, you see he's actually really nice. And even prior to that, his adorable daughter Eliza says that while he "talks like a hooligan, he'll never leave my side." Awww.
- Corpse Party has Yoshiki Kishinuma. He enjoys teasing Satoshi, but so does everyone else, and he's a pretty decent guy overall.
- Amounts of casts in Inazuma Eleven look like thugs and bullies like Someoka, Builder, Tobitaka, and other recruitable characters whose faces are just plain scary and weird. To put it, Someoka looks very similar to Garret example above.
- Rocko Sasquatch in The Inexplicable Adventures of Bob.
- In Axe Cop, all mermaids are good but have mean-looking faces, apparently because they thought scowls indicated happiness and smiles indicated anger. Axe Cop, unaware of this, murders one by accident. After learning that mermaids are all good and that this is the first time he ever killed a good guy, he immediately breaks down in tears.
- Rondo Hatton got into film because his acromegaly made his face look very thuggish. He's even got an award made in his honor.
- Pope Emeritus Benedict XVI, who bears more than a passing resemblance to Emperor Palpatine of Star Wars. Cue massive Memetic Mutation once he was chosen.
- Real Life example: Joe Raposo, best known for writing songs for Sesame Street, is described as looking and sounding "like a tough Italian street fighter from an urban ghetto."
- Singer Aaron Neville appeared briefly in one movie as "Man with gun," an intimidating character the hero confronted in a slum area. His voice has been described as the voice the angels wish they had.
- Mexican American actor Danny Trejo combines this with Badass Mustache and perpetual Death Glare to make him the go-to guy to play Latino thugs in Hollywood. Ironically, he really was a thug until he turned his life around. Now he's an actor and a motivational speaker and one of the most well-respected men in Hollywood, with everybody who works with him talking about what a great person he is.
- Billy McGuinness, rhythm guitarist, harmonica player and backing vocalist for the Irish band Aslan looks tough, but is actually very friendly. To look at him without hearing their music, one would think the band play a harder form of music than the radio friendly melodic rock they do. As the most noticeable member of the band it's no wonder he handles most of their interviews.