Donquixote Doflamingo is known for making this kind of face, usually when he laughs. He's also a notorious Ax-Crazy pirate.
Caribou is another, and he can come across as even more maniacal than Doflamingo. He also likes to lick his own hair while sporting a Slasher Smile.
Bellamy the Hyena is another pirate who is often seen sticking his tongue. In fact instead of the more traditional skull, his personal jolly roger is a pair of lips with a tongue sticking out paired with the crossbones. It's all makes sense since he's Doflamingo's subordinate.
Anime episode #49. In a Flash Back Kaien Shiba is possessed by the hollow Metastacia and turned into a vicious, deranged killer. At one point he sticks out his tongue at Rukia, as seen here.
The Fifth Espada, Nnoitra Gilga, not only likes to do this, but he also has a reason for it: the number signifying his Espada rank is tattooed on his tongue. As a bonus Nnoitra also shoots his Cero from the tip of his tongue.
When Nianzol first reveals his presence, mocking Shutara for accusing Yhwach of insolence, his grin is accompanied by his two tongues lolling out in a W-shape. His Sternritter letter is 'W'.
Naruto: Orochimaru, being a humanoid snake, does this often. And it's all intimidating.
Yami Malik from Yu-Gi-Oh! contorts his tongue in several different ways. It's very, very creepy.
The Joker from The Dark Knight licks his lips while he talks a lot. Word of God states that this was a result of Heath Ledger being annoyed by the feeling of the scar prosthetics and unconsciously licking at them because of it and after seeing him do it a few times with the full make-up and finding it seriously creepy, they decided to just make it part of the character.
In Highlander, the Kurgan does this to intimidate a group of nuns in a church.
For that matter, the other half of the orignal Diabolic Khaos, Delirious is also known to let his tongue dangle on occasion or excessively lick around his face/mask.
The Undertaker is an electricity controlling, teleporting, implacable zombie who not only threatens his opponents with defeat but also their lives and souls. He likes to stick out his tongue◊ during his rest in peach pin.
Tasha Simone, especially when using the stomach claw.
Psycho Clown of AAA's Psycho Circus just doesn't know when to keep that thing in his mouth.