Even if they did well, there are some people you can’t see as anything but “that character”.
For me examples
In Twilight and seeing Robert Pattinson, all I could think was "Harry stop whining, Cedric is alive.. Although for some strange reason he seems to glow in sunlight.
I chortled everytime I saw David Scwhimmer in Band of Brothers, hey its Ross.
Ted Danson in his minor role in Saving Private Ryan. I kept subconsciously expecting him to say something funny.
George Reeves in From Here to Eternity: “Hey, what’s Superman doing at Pearl Harbor?”
He also tried to romance Scarlett O’Hara in “Gone With the Wind.”
I THINK it was “Memphis Belle,” but I’m not sure… it was a WW2 movie, a serious one, that featured Ed O’Neil (Al Bundy). There was nothing wrong with his performance, but I just couldn’t take him seriously.
I had a hard time with him playing Sgt. Joe Friday. I think his acting was good, but, yeah.
Tim Curry in pretty much anything. No matter what he’s in I can’t help but picture Dr. Frank-N-Furter.
It was kind of funny seeing him as the prudish professor in “Kinsey.” The whole time I was thinking this is the guy who once pranced around in fishnet stockings and a bustier. Who’s he to lecture anyone on sexual mores.
In The Spanish Prisoner, O’Neil was an FBI agent and Steve Martin was a grifter, but Mamet was deliberately messing with the movie-goers’ minds.
As a child, I saw Dustin Hoffman in the movies Dick Tracy and Hook, and I’d heard that he’d been a really lame comedy called Ishtar. I thought he was a comedic actor. :smack:
It took a while to get used to him in serious roles. Point in fact, I think I still haven’t. He may have been a good dramatic actor during the 70s, but past that point he’s always seemed to be a bit of a parody of himself, going about chewing the scenery. I think he’d do better in comedic parts.
Speaking of Joe Friday, there was Jack Webb when he played other roles (most notably as William Holden’s best friend in Sunset Boulevard and as a comic sidekick in The Last Time I Saw Archie)
Wilfred Brimley, both in The Firm and Hard Target.
Wahile watching Hard Target my boyfriend at the time and I kept saying the oatmeal tagline in a bad cajun accent.
Hugo Weaving. He’s a great actor, but when I saw LOTR: The Fellowship of the Ring, all I could think was “Holy crap - Agent Smith is the king of the elves!”.
Thomas Gibson. He does a great job as Agent Hotchner on ‘Criminal Minds’, but I keep expecting to see Jenna Elfman show up at any second (he was Greg in ‘Dharma and Greg’).
Have you seen Priscilla, Queen of the Desert? 
FWIW, almost none of the examples given so far involve true typecasting.
True typecasting:
[ul][li]ugly guy as villain (e.g., Jack Palance in Shane)[/li][li]square-jawed guy as hero (e.g., Harrison Ford in Blade Runner)[/li][li]curvaceous blonde as whore (e.g., Ona Munson in Gone with the Wind)[/li]black person as servant (e.g., Eddie Anderson as Rochester)[/ul]
And both of these movies are much funnier if you saw Priscilla: Queen of the Desert first.
ETA: Curse you, Freudian Slit!
There is something ironic in a reference to Weaving’s LOTR role followed by a reference to Jenna Elfman. 
Of course, the all time greatest bit of unintentional typecasting is George Takei. Prior to Star Trek, his most memorable role was in the movie PT-109, in which a Japanese destroyer basically runs over Kennedy’s PT boat.
He played the destroyer’s helmsman.
For my wife, THE DEAD ZONE ground to a screeching halt right when it was supposed to ratchet the intensity up a notch: the ultimate nightmare scenario is President Martin Sheen, that brilliant and hardworking economist who’ll shrug off personal illness while bringing peace to the Middle East? Who else should responsibly fix our nation’s energy policy in between overseeing the minimum necessary use of military force?
Superman at Pearl Harbor is weird – but Jed Bartlett is supposed to be in the West Wing!
I tried to watch Garden State once, and was unable to get through it because Zach Braff is JD from Scrubs. (And because it’s just not that great…)
Sarah Michelle Gellar in The Grudge. C’mon, Buffy – one little ghost gets you worried? Sheesh!
“Des men afta’ you fo’ business or fo’ pleasah’?..Diahbeeatus.”