I’d go for another of Giamatti’s roles - as the monstrous Dr. Eugene Landy in Tender Mercies where he plays Brian Wilson’s psychologist/psychiatrist.
Ahem. Love and Mercy. Good pick, though.
Don Logan - “Sexy Beast”
petty, manipulative husband in “Knife in the Water”
protagonist in “Goalie’s Anxiety at Penalty Kick”
do androids count? (Ash in “Alien”)
two Welles - Charles Foster Kane, and in “Touch of Evil” Hank Quinlan.
despicable lite?
Steve Martin as the con in “The Spanish Prisoner”
maybe Charles Fotser Kane actually
Bob Roberts
I’m guessing Frank Booth in “Blue Velvet” wouldn’t qualify for being just too outright loony/scary. (Well, in a funny way.) (To me anyway)
Perhaps the most despicable character I can think of is maybe the Charles Coburn dad to the Nick Nolte son in “Affliction”.
Honorable mention to the brief appearances of Dr. Brodsky, the jolly commandeer of the Luduvico treatment in “A Clockwork Orange”.
Oh, how could I forget Grandpa Joe from Willy Wonka and the Chocolate Factory? Lives in bed for 20 years while Charlie’s mom is the sole breadwinner feeding 4 elders and Charlie. He gets a ticket to a chocolate factory and suddenly he’s dancing!
Stealing from his mother was pretty bad. I wouldn’t say the movie portrays him as sympathetic from that point on, though. More pathetic than sympathetic. And he did help his friend Jack cheat on his fiancée and lie to Stephanie (Sandra Oh). He hid his alcoholism under a layer of wine snobbery, and sometimes acted like a real jerk (like when the pourer at a winery refused to give him a full glass).
I don’t think all this makes him as despicable as most of the of the other characters named here, but I don’t see him as sympathetic, either.
I did love the movie, though.
“Do yeah need any money?” The real tragedy is the mom knows her son, but also not really, “Did you ever get back together with your ex wife? I loved her, Miles, she was so good for you.”
He’s a complicated character and so are the people around him so no one lives in a morally pure universe. Perhaps why it’s called Sideways…
Devonia, the babysitter in Beethoven who lets the younger daughter almost drown in the pool, tries to hush up the incident, and finally blames the mother to her face for the child’s lack of “discipline.”
Question: Are we strictly limited to movie characters only? Are TV characters not allowed?
Because I think Lester Nygaard from Season 1 of the TV series is even more despicable than Jerry. Spoilers for those who haven’t seen it: Lester straight up murdered his wife, framed his brother for it, had sex with Hess’s widow under the pretext that he would expedite her life insurance payout in exchange, even though he already knew the claim had been denied, and then got his second wife killed by using her as a decoy when he knew Malvo was in his office.
Sure, why not? I don’t see any reason to limit it to movies.
Frank Dixon in The Terminal.
William Shatner as Adam Cramer in The Intruder deserves a mention
Bill Sikes as portrayed by Oliver Reed in Oliver! the movie musical. He is an intimidating, violent, abusive brute. Sikes abuses his dog Bullseye, who remains loyal to him, until the very end when Sikes goes too far.
KAHN!
Also the boss in Office Space.
Nightcrawler may be the best portrayal of a sociopath I’ve ever seen. In the past they’ve been portrayed as crazy wildcards that cannot be trusted so while evil would never be able to form much less head something like a DC Universe crime syndicate.
But Jake Gyllenhaal’s character will remind you of a person you went to school with…
Since we’ve opened it up to TV, I’ll nominate De’Londa Brice in The Wire:
After her husband Wee Bey was sentenced to life in prison for murder, and the Barksdales cut off her money, she decided her 14-year-old son Namond should become a crew chief in the drug business to support her, the way Wee Bey used to. At one point, when Namond had been arrested and his teacher Bunny Colvin took him home for the night so Namond wouldn’t have to go to jail, De’Londa expressed scorn that he was afraid to go to “baby booking” and told Bunny to “leave my son the fuck alone.” She made things so bad for Namond for not being hard enough that he eventually decided he couldn’t go home any more.
Brianna Barksdale was bad, but not quite as bad as De’Londa, at least in my opinion.
Office Space was a historical documentary about a place I used to work, I am sure of it. Right down to the boss with suspenders and a Porsche.
The series Game of Thrones is full of candidates, I think Ramsay Bolton, who takes genuine joy in rape, torture, and murder is the most despicable.