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There have been many great artists who have captured our beloved J in many great ways. But I guess, ultimately, my favourite would have to be Brian Bolland. Brian Bolland, a wonderfully talented artist, set the standard for visual depictions of Joker with his work in The Killing Joke. So what makes his Joker so great?
As always, click an image to see it full-size!

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The Realism

Remembering that Bolland's depiction came straight on the heels of the seventies when Joker was being portrayed in an intensely cartoonish fashion - goofy and whacky rather than threatening and wild (with the exception of a few notables such as Laughing Fish). Bolland's beautiful, graceful art style showed a Joker we could really believe in - his long, lanky body in proportion as that of real tall men, with a realistic facial structure - yet retaining all the extreme elements that make J, J!

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The Lunacy

While we could all see that beneath Joker's chemically altered colouring and wild grin there once was a 'regular' man, Bolland's depiction faithfully demonstrated Joker's madness as well. The slightly boggling, crazed eyes; the mirthless grin; the manic, wild hair. His Joker is SCARY, menacing, frightening.
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The Emotion

Rather than having a 'perma-smile', Bolland's Joker is capable of a range of facial expressions. Intense and compelling ones, reflecting the wild, violently swinging moods of our Clown Prince. Just as Joker's psychotic smile is truly chilling so too is his anguished grimace sympathetic and heart-stabbing. And even as his appearance is frightening, there’s an air of mischief about it as well.
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The Dignity

Whilst I appreciate the use of extreme visual styles to depict the essence of a character, I do get weary of the thin-to-the-point-of-frailty, looooong chinned, knock-kneed caricature and the mincing, posturing, limp-wristed cliché some artists do. Joker has effeminate, and delicate habits and attitudes. He can be fey. He can also be over the top and melodramatic, as well as classically ostentatious and theatrical. He is long and lanky. But he is always dignified. He is not a buffoon. His dignity is important to him. Bolland's Joker retains this dignity whilst also preserving the slimness, the slight effimacy and the theatrical flair. And Joker, whilst effeminate, is not foppish. Bolland's Joker maintains a dignified, non-posturing and even non-aggressive masculinity.
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The Theatrical Dandy

Joker is a consummate showman, and every showman knows everything counts. Every little detail is significant. From mannerisms and speech to the shine of the shoes and the cufflinks selected, it is all vitally important to the final effect. Bolland's Joker's suit fits him perfectly in the colours he adores, his spats are perfectly white, his unruly hair is combed and pomaded (if regularly escaping - like himself, Joker's hair is something of a rebel), his tie is neat and even. It reflects Joker's own care taken with his schemes and his awareness of the world as his stage.
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Schmexiness

Bolland's Joker is hot. I've always had this thing for tall, lanky, slightly effeminate men with aquiline features and Bolland's Joker is pretty much a perfect embodiment of that physical type. His Joker's eyes practically gleam with maniacal intelligence and while slim, he's not weak or emaciated. He's just naturally lean. Bolland's Joker has a real presence and even as the smile is frightening it also draws us to it like a magnet. It's so knowing and so sly and so delighted. His posture and attitudes indicate this Joker is dexterous and deft, agile and unpredictable.
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Harley's Haven is dedicated to the memory of Heath Ledger, an actor who devoted much to the role of The Joker.