3. Michael Clayton (Michael Clayton)
George Clooney is back in the list as the titular Michael Clayton in Tony Gilroy’s 2007 thriller. Attorney Clayton is a fixer of sorts for law firm Kenner, Back and Ledeen. He uses contacts with city officials and local police to cover up indiscretions by the firm’s corporate clients, rich men who exploit the people around them, steal, and even kill people.
If this isn’t bad enough, Clayton has his own personal demons. An alcoholic gambler with seemingly few morals left, he owes a huge sum of money to a loan shark thanks to his own brother’s drug addiction. Not the kind of man you’d want looking after your affairs.
2. Kevin Lomax (The Devil’s Advocate)
In Taylor Hackford’s 1997 thriller, Keanu Reeves plays a ruthless young attorney whose win record is everything to him. Lomax has never lost a case, and when he comes close to doing so, he shakes off his moral shackles and successfully defends a high school teacher accused of molestation.
Lomax knows his client is guilty, but with his will to win insatiable, he tears apart the victim’s mother on the witness stand. This willingness to embrace the darkness brings him to the attention of a powerful New York lawyer, and Lomax finds himself seduced by success and excess, as his new boss watches on…
1. John Milton (The Devil’s Advocate)
The lawyers on this list all have major flaws, both personal and professional. Some are guilty of defending criminals and miscreants. Others for exploiting the vulnerable and mistreating the people around him. Al Pacino’s John Milton corrupts hotshot young lawyer Kevin Lomax. He encourages him to represent scum and lowlifes, leads him into a lifestyle of decadence and excess.
Milton causes Lomax’s relationship with his wife to suffer, leading to Lomax declaring his wife insane. These are not the reasons why Milton is our number one shadiest lawyer, however. Many consider lawyers to be evil and demonic, but Milton goes one further. He is, literally, Satan.
