Lionel Granger (David Thornton)
Marrying Cyndi Lauper is the smartest thing David Thornton ever did. In second place: taking the role of consummate asshole Lionel Granger, one of the biggest turds in the New York judicial system. Slick, unethical and easily up for any legal challenge, Granger once accused St. Olivia Benson (Mariska Hargitay) of murdering a sexual sadist that forced his female victims to marry him in a dungeon (turns out it was Jacqueline Bisset...or Samantha Mathis). He has even joined forces with fellow scumbag Roger Kressler (Ned Eisenberg), playing duplicitous defender to a pack of homicidal teenage girls who beat one of their friends to death and proceeded to stab her corpse hundreds of times with a pair of manicure scissors. His defense? Extreme emotional distress. Stay classy, Granger.
Roger Kressler (Ned Eisenberg)
One of those characters that is so off-putting, the mere sight of them alighting from one of the courthouse elevators can send you frantically searching for a piece of drywall to punch. Kressler is as slimy as they come, standing up for serial killers, pedophiles, teenage sadists and, virtually, any scumbag with money. One prime example of said sliminess occurs in S2 episode 'Closure.' Harper Anderson (Tracy Pollan) accuses Kessler's client of defending a serial rapist.
Anderson: 'I've seen you in court, Mr. Kessler. You're a very famous man. You're gonna burn in Hell.'
His retort: 'I'm Jewish, Ms. Anderson. There is no Hell.'
NUMBER OF EPISODES: 21
Matthew Braden (Steven Weber)
Matthew Braden is a total dirtbag. Even Elliot Stabler thinks so ("How do you sleep at night?") This guy has defended some incredible lowlives: A gangster on trial for murdering a 14 year-old boy, in addition to witness intimidation. Another scumbag (played by Ludacris) is accused of murder, and Braden gets him off by muddying the reputation of Detective Tutuola (Ice-T...who wasn't too happy about it.) Fortunately, he pops up very infrequently.
NUMBER OF EPISODES: 3
Milton Schoenfeld (Rob Bartlett)
OH! OH! MAN! I hate this guy. He virtually oozes dislikability. All of his clients are scum, including the one where Henry Winkler's character arranges to have his wife (Mary Beth Hurt) beaten to death so he can run off with her money. Or the episode where Bruce Davidson's character is accused of impregnating a comatose woman, and he tries to get Schoenfeld to use stem cell research as a viable defense? So smug. And his little moustache just makes you want rage.