Catherine Zeta-Jones in Chicago.

And Louise Fletcher as Nurse Ratched in One Flew Over the Cuckoo's Nest. But that exhausts the list of female Academy Award winners with no redeeming qualities. Even Monster, about a serial killer, had Charlize Theron give Wuornos some redeeming qualities -- she tried to go straight, she protected her girlfriend, etc.

Male villains have a much better chance of winning an Oscar. And flawed male villains, from Walter Brennan as Judge Roy Bean in The Westerner and George Sanders as Addison DeWitt in All About Eve to the others named here, have a direct pathway to the Oscar.

I'm kind of on the fence about Faye Dunaway's network executive in Network.

Faye Dunaway's character may have had a name (Diana Palmer), but the script actually had her playing television itself, not a real person. When Paddy Chayevsky's script had William Holden's character Max tell Diana that she was television, he meant it literally -- her character really was the personification of TV.

That's one way of looking at it. The reason I was on the fence about it is that Network goes so deep into satire that most of the main characters are caricature. No one is really this way but for the purposes of making a point and playing out this drama these players will go to these extremes, absurd as it seems the absurdity is much the point.

William Holden as Max is there to help you understand, he's your real person giving you perspective. Everything else is showbiz.

I agree about Max. Other than Diana, the rest of the people are show-biz stereotypes. But I stand by my interpretation: Diana is TV itself, from the amorality to the lack of interest in message (because, as Marshall McLuhan said, the medium itself is the message).

as mentioned above, quite a few.
There's also Denzel Washington in Training Day, Ruth Gordon in Rosemary's Baby, F. Murray Abraham in Amadeus, Jeremy Irons in Reversal of Fortune.
That's just the winners, haven't gone through the nominees, yet. And truthfully anything before 1960 and I'm kinda lost.

Angela Lansbury in "Manchurian Candidate" comes to mind as a losing nominee (to Patty Duke).

Julie Andrews in "Mary Poppins". And then she was nominated again the following year for playing an even more despicable character in "The Sound Of Music"!

<<shudder>>

is who the actor/performance was up against.

Shelley Winters's competition consisted of two unfamiliar British actresses who appeared in what was basically a filmed stage performance of "Othello" (one was Maggie Smith, not yet famous), plus the one-dimensional Mother Superior in "The Sound Of Music" and Ruth Gordon as Natalie Wood's mother in a critical bomb.

"A Patch Of Blue" by contrast was critically well-received, with five nominations and the social consciousness aspect going for it -- and Shelley Winters was a popular Hollywood actress playing against type. Not hard to see why she won.

Rose-Anne is a great character who could have walked right out of a Tennessee Williams play, and this was at the time when the Hays Production Code was finally breaking down. People wanted to celebrate a fine performance, especially since Brando had NOT won Best Actor for Stanley in A Streetcar Named Desire.

However, while Inside Daisy Clover may have been a critical bomb, the movie's negativity toward studio executives made it popular in the Hollywood of the 1960s. Even Robert Redford's insistence that his character be changed from homosexual to bisexual didn't change that. Plus, Ruth Gordon was a very popular actress. The winner wasn't a foregone conclusion by any means.

However, I do agree that the two Othello nominees were out of the running. The less said about Laurence Olivier in blackface, the better.

LAST EDITED ON 01-29-13 AT 01:13 AM (EST)

I didn't say Winters's win was a foregone conclusion, I said it's not surprising that she won, taking all else into consideration, which seems to be your point as well. I wasn't implying her performance wasn't worthy; it was very good.

And Ruth Gordon was nowhere near a popular film actress in 1965; "Inside Daisy Clover" was her first film appearance in roughly 20 years. Her Hollywood reputation at that point rested on her screenwriting credentials (albeit she had continued to act onstage).

True. Remember, though, that Gordon created the role of Dolly Levi on stage in the 1950s (and was nominated for a Tony for it), she wasn't used for the movie based on it (which starred Shirley Booth instead).