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18 Sleazy Movie Lawyers

The Dark Knight (2008)

The Sleazy Lawyer: Two-Face, more of an ex-lawyer. Originally known as district attorney Harvey Dent, and celebrated as the White Knight of Gotham, Dent’s determination to do good is twisted into something evil by The Joker, and he becomes Two-Face.

Defending: Gotham and its residents. Dent believes Batman’s doing more harm than good, and wants him gone.

Did They Win? Sort of. Gotham has now turned against Batman, believing him to be an anarchic chaos-lover, while Dent’s reputation remains mostly intact.

Fatal Flaw: Trusting The Joker. Stupid.

Chicago (2002)

The Sleazy Lawyer: Billy Flynn who, like all the best lawyers, has a way with the words. And the ladies, as it happens. Flynn acts as the personal defence attorney to the residents of Cook County Jail – who all happen to be female.

Defending: Mostly naive young murderess Roxie Hart, who has been banged up for shooting her lover Fred Casely.

Did They Win? Yep, thanks to some clever truth-hair-splitting (and a variety of catchy musical numbers), Flynn successfully has Roxie proclaimed innocent.

Fatal Flaw: Uh, the ladies of course. Though he makes a pretty penny out of them.

The Devils Advocate (1997)

The Sleazy Lawyer: John Milton, who lives by the saying “Better to reign in Hell than to serve in Heaven”. He’s a partner of high-end law firm Milton, Chadwick & Waters. Oh, and he’s Satan.

Defending: Milton specialises in freeing wrong-doers in hard-sell cases, including that of corporate billionaire Alexander Cullen, who’s accused of murdering his family.

Did They Win?
Thanks to new recruit Kevin (Keanu Reeves), Cullen is acquitted – even though they discover Cullen is guilty.

Fatal Flaw: Free will, which saves Kevin from Satan's gnarly claws in the end.

The Godfather (1972)

The Sleazy Lawyer: Tom Hagen, who’s more of a crooked lawyer than an all-out sleazeball. Why? Well, he was unofficially adopted into the mobster Corleone family as a bruised, beaten child. Now, he’s their man on the inside.

Defending: The Corleones – to the death. Hagen goes about insidiously bribing (check out the deleted scene in which he all-but threatens to expose a Hollywood star as a heroin addict) and scaring (horse head in bed) those who go up against the family.

Did They Win? Just about every time; the Corleones always get their way in the end.

Fatal Flaw: Hagen has a mistress, something that works against him when Michael uses the information as a threat in The Godfather II .

Liar Liar (1997)

The Sleazy Lawyer: Fletcher Reede loves his job, and will do anything to win a trial – even if it means lying through gritted teeth. Which is what he does in his everyday life as well. Until his son makes a birthday wish that, for just one day, his father is unable to tell a lie.

Defending: Samantha Cole (Jennifer Tilly) during her divorce case, who’s willing to commit perjury to win. The defence is made trickier by the ‘no lying’ birthday curse that Reede’s suffering under.

Did They Win? Luckily for Reede, he finds a way to win the case without lying. There’s a Sesame Street episode in there somewhere, we’re sure.

Fatal Flaw: Uh, lying. And not doing right by his son. Bad dad.

Carlitos Way (1993)

The Sleazy Lawyer: Dave Kleinfeld is the epitome of sleaze. A greasy, money-grabbing urchin, he stole $1m from his mob boss client, and slits throats without batting an eyelid.

Defending: Carlito at first, managing to release the thief from a lengthy jail sentence by exposing a technical flaw in his sentence. Most of his ruthless activities take place outside the courtroom.

Did They Win? Not really. He may have gotten his hands on a load of money (and covered them in blood in the process), but Kleinfeld never really wins.

Fatal Flaw: Trusting in Carlito. When he’s in the hospital, Carlito assists in Kleinfeld’s murder by unloading his gun so that he has no protection against a mob assassin.

The Accused (1988)

The Sleazy Lawyer: Kathryn Murphy, who becomes sleazy by proxy thanks to her lenient stance when it comes to gang rapists. She’s assigned the case of Sarah Tobias (Jodie Foster), who was raped outside a bar by numerous drunk men.

Defending: Rapists, essentially. Even though she’s the DA, Murphy is convinced by her peers to let the rapists plead guilty to reckless endangerment. If they did so, they’d get a sentence that permits them to have parole in less than a year.

Did They Win? Of course not. Sarah takes her case to different lawyers, and wins.

Fatal Flaw: Peer pressure. Murphy gives in to the demands of her superiors.

Body Heat (1981)

The Sleazy Lawyer: Ned Racine, who’s having an affair with Matty (Kathleen Turner), the wife of an extremely wealthy businessman. Greedy and conniving, Racine has no boundaries when it comes to getting what he wants.

Defending: Matty’s future. When they learn that if she divorces her husband she’ll get a mere fraction of his fortune, Racine and Matty plot to murder the businessman.

Did They Win? Afraid not. Paranoia and suspicions escalate after Racine kills Matty’s husband, then he learns that Matty never really loved him – and might not even be who she says she is. Messy indeed.

Fatal Flaw: Love. It makes fools of us all, and particularly Racine, who fell for Matty’s charms instantly.

The Rainmaker (1997)

The Sleazy Lawyer: Leo F. Drummond, an arrogant defence attorney who is surrounded by a ring of equally ruthless and scheming lawyers. Nothing is off limits for Drummond, who has never heard the words ‘fair trial’ in his life.

Defending: A high-profit, corrupt health insurance company, who let a young man suffering from leukemia die by refusing to fund his therapy.

Did They Win? Drummond loses what must be his first ever courtroom battle when he comes up against young graduate Rudy Baylor (Matt Damon).

Fatal Flaw: Playing dirty. Drummond underestimates Rudy’s intelligence, and is shown up in court during a particularly embarrassing incident involving phone tapping.

Judgment At Nuremberg (1961)

The Sleazy Lawyer: Col. Tad Lawson, who skirts sleaze without ever truly giving into it as a completely tactless military prosecutor. He uses shock tactics to make his point.

Defending: Justice and humanity, seeking to condemn four judges who stand accused of crimes against humanity during World War II.

Did They Win? They did – the four judges are all sentenced to life imprisonment.

Fatal Flaw: Passion, which sometimes gets the better of him.