The Lighter Side: Hollywood's best, worst and most bizarre lawyers

by NZ Lawyer07 Mar 2014
In light of this week’s Academy Award ceremony, we thought we’d take a look at Hollywood’s top fictional lawyers. The following list comes from (not to be confused with, a legal news and marketing site based in the US and gives us the good, the bad and utterly bizarre of cinematic counsel…

The good

Perry Mason in the TV series Perry Mason
Played by: Raymond Burr
Perry Mason is one of the most classic lawyers in television. He is an excellent defense attorney who never stops working until he has discovered truth. Mason is known for his uncanny ability to cajole confessions out of witnesses while they are on the stand. Perry Mason was not just a good person; he was good at his job.
Elle Woods in Legally Blonde
Played by: Reese Witherspoon
Elle Woods is introduced as a silly and shallow sorority girl, but turns out to be a surprisingly capable attorney by the end of the film. Although she works hard in school, most of her legal prowess comes from her less conventional training. She uses her expertise in fashion and hair styling to prove that two of the witnesses in a murder case are lying. Her unique set of skills help set an innocent woman free and send the real killer to prison.


Marylin Delpy in The Social Network
Played by: Rashida Jones
Marylin Delpy is a pretty small character in a big movie, but she is observant and smart, and takes the time to make a connection with Mark. She is honest and straightforward with him and because of this, she is one of the few people he listens to.
The bad

Billy Flynn in Chicago
Played by: Richard Gere
Some may argue that Billy Flynn belongs in the good category, since he is particularly good at his job, but he is a particularly bad person. He is clever enough to get two of his clients off the hook in one trial, but he does it by fabricating evidence, manipulating people, and lying profusely. All Billy Flynn cares about is money, so instead of using his skillset to do good, he squeezes money out of sad, cuckolded husbands and uses it to get murderous women out of jail and back on the streets.

Jackie Chiles in Seinfeld
Played by: Phil Morris
Jackie Chiles represents Cosmo Kramer in a number of cases. One time they sue a coffee shop and another time they accuse Sue Ellen Mischke of causing Kramer to crash his car. Jackie is known for his use of long adjectives like lascivious, salacious, and egregious, but his extensive vocabulary doesn’t help him win cases. This is largely due to Kramer, who manages to muck up the works, but the fact that Jackie keeps taking him on as a client demonstrates a serious lack of judgment.

Denny Crane in Boston Legal
Played by: William Shatner
Like Billy Flynn, Denny Crane's a darn good lawyer (in the series, he claims to have never lost a case). However, he also shoots one of his own clients, makes sexual advances on judges' wives (and anything else with two x chromosomes) and believes gun control is for Communists. 

The bizarre

Barry Zuckerkorn in Arrested Development
Played by: Henry Winkler
Barry Zuckerkorn is such a bad attorney it is baffling. He is constantly unprepared and uninformed. In one case, he is so surprised at the number of charges against his client that he runs away; in another case he shows up without having read the plea bargain his client was offered. On one occasion, he encourages the Bluths to steal evidence from the prosecution, and when Kitty goes missing, he tells them to lie to the police.
Zuckerkorn’s ineptitude extends to the rest of his life as well. One time, he is late for a hearing because he was a defendant in another court case the same day. His bizarre preferences and bad choices mean he is often embroiled in legal trouble himself. A lawyer’s personal life doesn’t always affect their work, but you don’t want an impaired driving defense lawyer who may be impaired on the job.

This is by no means a definitive list and many good, bad and bizarre lawyers were left out, so feel free to add your suggestions and favourites in the comments box below.


  • by jfwd 7/03/2014 10:44:29 a.m.

    Dennis Denuto (The Castle) so belongs in this list, "It's just... the vibe... of the thing".

  • by jmmorrell 12/04/2014 2:55:47 a.m.

    My Cousin Lenny. Don't recall the names of the key characters, nor the names of the actors who played them. Winning defense attorney established a crucial timeline by recalling a witness' testimony that "everybody in the south knows you cannot cook grits right in less than 25 minutes". . . or something like that.

    Its the only line in the film that stuck with me over the years. Imagine that!

  • by Nick Rout 14/04/2014 11:57:38 a.m.

    How could you leave out Breaking Bad's Saul Goodman.

    So good they are making a spinoff "Better Call Saul"