Joshua already laid out the most badass attorneys of all time. But what about the just plain bad? Here’s a countdown of some of the most vile, evil, and corrupt lawyers ever to enter the popular imagination. From drug lawyers to mafia bosses, let’s just say that none of the attorneys on this list aced their Professional Responsibility exams.

6. Tom Hagen, The Godfather Parts I-II

“Now we have the unions, we have the gambling; and they’re the best things to have. But narcotics is a thing of the future. And if we don’t get a piece of that action, we risk everything we have. “

He may not be a wartime consigliere, but Corleone family attorney Tom Hagen knows a thing or two about a thing or two, capice? Advisor to two generations of mafia dons, Hagen is loyal and capable. He arranges any number of hits and guides his mob bosses through several turf wars and acquisitions. He negotiates with crooked judges and corrupt senators and intimidates casino owners and studio heads. He even takes over as acting Don in The Godfather Part II. He’s an able attorney, but if you get on his bad side you just might wake up next to the severed head of your favorite horse.

5. Billy Flynn, Chicago

“Give ‘em the old double whammy
Daze and dizzy ‘em
Back since the days of old Methuselah
Everyone loves the big bambooz-a-ler”

As defense attorneys go, Billy Flynn is a success. He gravitates toward the limelight and seems to specialize in defending the most salacious and tabloid-friendly clients, getting even the most blatantly guilty an acquittal. Most of his litigation tactics seem to revolve around snapping his fingers dancing a softshoe, and jazz hands, which may or may not be sound legal practice but sure does wonders with his all-female clientelle. They must teach those techniques in advanced Trial Advocacy.

4. Harvey “Two-Face” Dent, The Dark Knight

“You either die a hero or you live long enough to see yourself become the villain. “

Unfortunately for crusading D.A. Harvey Dent, his words turned out to be true. Despite being the only criminal prosecutor on this list, it isn’t long after he loses half of his face to a horrific disfigurement before he goes on homicidal crime spree. Whether on a specifically-targeted revenge spree as in the The Dark Knight or the more generalized villainy of the comic books, Harvey Dent is one bad dude with two  faces. The tragedy of the character is that he starts off as a crusading force for good, but ends up as a punching bag for a rich orphan in a bat costume.

3. Wolfram & Hart, Angel

“Our firm has always been here…in one form or another. The Inquisition. The Khmer Rouge. We were there when the very first cave man clubbed his neighbor. See, we’re in the hearts and minds of every single living being.  See, the world doesn’t work in spite of evil. It works because of it.“

An evil law firm with offices all over the world and in several dimensions, Wolfram & Hart were the long standing antagonists whose apocalyptic plans made life difficult for vampire with a soul Angel. The Senior Partners are unspecified demons from a hell dimension, the firm keeps a team of ninja assassins on retainer, has an in-house blood sacrifice division, and makes their associates sign employment contracts that keep their souls billing hoursfrom the afterlife. So just like any other BigLaw firm, really.

2. Maurice Levy, The Wire

Maurice ‘Maury’ Levy: You are amoral, are you not? You are feeding off the violence and the despair of the drug trade. You are stealing from those who themselves are stealing the lifeblood from our city. You are a parasite who leeches off…
Omar: Just like you, man.
Maurice ‘Maury’ Levy: …the culture of drugs. Excuse me? What?
Omar: I got the shotgun, you got the briefcase. It’s all in the game though, right?”

Counsel for Marlo Stanfield, The Wire’s most infamous drug kingpin, Maury Levy epitomizes the amoral sleaze that crusts up at the bottom of the legal barrel. The Wire is rightly praised as the deepest, most uncompromising peice of modern literature and it doesn’t pull any punches in its portrayal of even the good guys, so a shyster like Levy is doomed to ignominy. He approaches the role of advocate with abandon, and he doesn’t leave any dirty tricks out of his arsenal. From advising his clients to kill potential witnesses to teaching a gangbanger tutorial on how to launder drug money Levy is everything a lawyer shouldn’t be. But he’s still less evil than…

1. John Milton, The Devil’s Advocate

“And as we’re straddling from one deal to the next, who’s got his eye on the planet, as the air thickens, the water sours, and even the bees’ honey takes on the metallic taste of radioactivity? And it just keeps coming, faster and faster. There’s no chance to think, to prepare; it’s buy futures, sell futures, when there is no future. ”

It’s hard to get much more vile than the source of all evil, Satan himself. He went to war with God. He tempted Eve. He has been bedevilling mankind since the beginning, but apparently he’s also a handy trial lawyer. As an attorney, he guides his firm in accepting ritual slaughter cases and isn’t afraid to do the dirty work himself. He personally dispatches the demonic muggers that make annoying managing partners go away. He may not be particularly clever at choosing inconspicuous aliases (seems like naming your earthly incarnation after a guy who is famous for writing a poem about you lacks a little subtlety even for the Prince of Darkness), but the fact that he is actively trying to instigate the End of Days makes him a very poor role model for would-be lawyers indeed.

Who are some evil lawyers you love to hate?

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2. 6 Most Badass Lawyers Ever