When an actor is constantly casted as a certain type of character, he is said to be typecasted. Examples of this include Bruce Willis being cast as the brash hero sent out to save the day, Seann "Stifler" William Scott being cast as the usual perverted jerk, Tom Hanks as characters with that "tame nice guy" image, Kelsey Grammar being cast as cultured and intellectual characters after "Frasier" (even The Beast and Sideshow Bob can be considered cultured and intellectual). When an actor is cast in a role completely different from his other films or other styles of acting, he is said to be playing against type.
I found myself very interested in this and I'm going to do a list of ten instances where I thought the actor playing against type really stood out. Of course, this is all subjective and the real point of this thread is to discuss actors that are typecasted or playing against type but I always like to kick these discussions off with a list.
10 (Click to reveal)David Schwimmer as "Captain Herbert Sobel" in Band of Brothers (2001)

How This Role Differs from the Usual: Dramatic turn from an actor normally doing comedy.
We'll kick this off with Ross G... I mean David Schwimmer. I've only seen Schwimmer in Friends and some motion pictures (I can count them with the fingers on my right hand alone). I didn't think his acting chops extended past Ross Gellar. Then I saw the HBO miniseries Band of Brothers. David Schwimmer plays Herbert Sobel, a DRILL SERGEANT of sorts and shouting insults and ordering everyone around. Though BoB is basically 10 hours long, I think Schwimmer only has like one hour of screentime. The first episode revolves around him, however, and his incredibly tricky character as Sobel isn't all that he seems to be. There's a shot of Sobel in there where he's watching the camera with this incredibly sad expression and that's what basically sold it to me.
Also, props to Ron Livingston (Office Space), another comedy actor, for turning in a dramatic performance in this same miniseries.
9 (Click to reveal)Steve Carell as "Uncle Frank" in Little Miss Sunshine (2006)

How This Role Differs from the Usual: Not the usual silly, lively Carrell role.
Okay, this one is a bit of a stretch because Little Miss Sunshine IS a comedy and Steve Carrell's role isn't a big overdramatic one and I sensed a trend in him doing something "smarter" than Brick in the Will Ferrell comedy, Anchorman, and as the gibberish-talking anchor in Bruce Almighty, when he did The Forty Year Old Virgin. He starts off as almost dead (maybe literally) in Little Miss Sunshine and works his way up to a dancing machine. When I first heard Carrell was going to play a gay suicidal uncle, I was like "What?" because I didn't really think he could pull off something like that, especially if it's in a comedy. But I thought him being casted in that movie worked well because we're accustomed to seeing the silly lively Carrell and here he is, somber and lifeless, and it helped that character stand out, especially as he progressed through the film.
8 (Click to reveal)Jim Carrey as "Truman Burbank" in The Truman Show (1998) and "Joel Barish" in Eternal Sunshine of the Spotless Mind (2003)

How These Roles Differ from the Usual: Dramatic turns from an actor normally doing comedy.
When I was a kid I couldn't get enough of Carrey. I watched Ace Ventura, The Mask and Dumb and Dumber numerous times. It got tiring eventually but I had a great time watching Carrey in his antics. Which kid didn't like those movies? Even though he was entertaining as hell, I guess I began to see Carrey as just the ultimate clown at a birthday party. Maybe he saw himself as that too and didn't hesitate to let Peter Weir cast him in his speculative comedy/drama "The Truman Show" as the titular character. As Truman Burbank, Carrey has toned down his antics a lot and concentrated more on his complex role. It worked for me and it was refreshing to see Carrey in a new type of role.
Then "Bruce Almighty" came and went and I thought he was back to old Carrey again. Then "Eternal Sunshine" came and his antics were gone again. He was playing a lovelorn introvert. I was pretty surprised at how well he acted this and how good he can do without his usual silly antics. However, he's had a few hard misses trying to play against type, though. Examples, The Number 23, The Majestic.
7 (Click to reveal)Jack Nicholson as "Warren Schmidt" in About Schmidt (2002)

How This Role Differs from the Usual: Does not have most of the trademark acting tics most Nicholson roles carry.
I'm not sure if I should have put Nicholson here because he's played characters in almost every film genre; comedy, drama, horror, crime, suspense. The thing about Nicholson, though, is that I always see him as Jack Nicholson (if I'm not seeing him as Joker). That's Nicholson yelling "HERE'S JOHNNY!". That's Nicholson saying "You make me want to be a better man." That's Nicholson saying "I don't want to be a product of my environment. I want my environment to be a product of ME." That's always been the problem with me. When you really boil it down, he's either playing a psychotic madman or a sleazy womanizer.
This is why About Schmidt stands out for me. He doesn't play either of those. He doesn't give that shark grin smile. He doesn't shout swears at people and starts raving. He's just a quiet old guy whose wife just died, just retired and is unsure about his daughter's fiance. I'm thinking that was Alexander Payne's work as he always seems to tone down comedians, such as Paul Giamatti in Sideways, Matthew Broderick in Election. It worked for me, though.
6 (Click to reveal)Bill Murray as "Polonius" in Hamlet (1999), "Raleigh St. Clair" in The Royal Tenenbaums (2001), "Bob Harris" in Lost in Translation (2003)

How These Roles Differ from the Usual: Dryer style of comedy, dramatic turns.
Murray is a weird person to put on this list because I don't think he's playing against type anymore. The roles you see him in now are the roles he's probably going to play for the rest of his career. I see the Bill Murray that played Peter Venkman in Ghostbusters, played the piano in Groundhog Day and whacking flowers in Caddyshack and the Bill Murray that played the lonely man in Lost in Translation, Broken Flowers, Life Aquatic, Royal Tenenbaums etc. as different actors. Maybe he got depressed for two years, grew a beard and decided he's not going to do What about Bob anymore.
5 (Click to reveal)Steve Martin as "Davis" in Grand Canyon (1991), "Julian Dell" in The Spanish Prisoner (1997), "Ray Porter" in Shopgirl (2007)

How These Roles Differ from the Usual: Dramatic turns from an actor normally doing comedy.
Steve Martin has always been a weird actor for me. When I watch him, he always strikes me as the type who knows how to drama but doesn't like doing it so he chooses to do comedy instead. He's always been one of the more "serious" comedians to me. That being said, I like his comedy (not his newer ones like Bringing Down the House and Pink Panther, though). I liked The Jerk (a lot), Bowfinger, Roxanne, Planes Tranes and Automobiles, Father of the Bride and these are what he's famous for. I don't really hear about the Steve Martin in Grand Canyon and The Spanish Prisoner, two dramas where he played characters of much more serious tones than his usual roles. Steve Martin playing a conman with a gun in a Davet Mamet movie? Check it out.
4 (Click to reveal)Adam Sandler as "Barry Egan" in Punch Drunk Love (2002) and "Charlie Fineman" in Reign Over Me (2007)

How These Roles Differ from the Usual: Dramatic turns from an actor normally doing comedy.
I hate Adam Sandler's comedies. He always seems to play the same character in every single one - himself. When you walk into Anger Management or The Longest Yard (for those of you willing to) you're always expecting to see the same guy - a young man who shouts a little, gives small "motivational" speeches once in a while, gets angry again and probably kicks something. Then I saw Paul Thomas Anderson's Punch Drunk Love. Paul Thomas Anderson directed Boogie Nights, Magnolia and There Will Be Blood and I don't think any P.T. Anderson movie had any acting that was nothing short of superb. Even though Punch Drunk Love can be considered comedy, I keep mentioning it and this role a lot because I find it to be paradigm of how a director can affect an actor's performance and how he can use that actor's lame regurgitated style to create something fresh. Anderson plays with Sandler's "angry" style to create a sensitivity and pain unknown to most Sandler characters.
3 (Click to reveal)Tom Hanks as "Michael Sullivan" and Jude Law as "Harlen Maguire" in Road to Perdition (2002)


How These Role Differ from the Usual:
Tom Hanks - Deviation from Hanks' image of being a pleasant or tame person.
Jude Law - Deviation from Law's "pretty boy" image.
I'm accustomed to seeing Tom Hanks acting as that guy who would light up a room when he enters it, whether he's acting like a little kid, a strange foreigner or a happy-go-lucky man-child. I'm also accustomed to seeing him isolated or physically suffering such as in Philadelphia or Cast Away. I'm not accustomed to seeing Tom Hanks as a hitman who acts cold and distant towards his child. But that's what we get in Road to Perdition. I don't know what made Sam Mendes cast Tom Hanks for this role (maybe star power?) but I found the role strangely fitting for Hanks.
As for Law, I believe he was relatively new at the time but I had not shaken off the Gigolo Joe image of him yet. I know everyone regarded him as a pretty boy of sorts, and I know how much good-looking actors/actresses (especially actresses) ugly themselves up for "good" Oscar-bait roles (Charlize Theron in Monster, Hilary Swank in Million Dollar Baby, Marion Cotillard in La Vie en Rose, the list goes on) but I don't think I had ever seen Law play a sinister sleazeball character before. Not like Harlen Maguire with his rotting teeth and receding hairline.
2 (Click to reveal)Elijah Wood as "Matt Buckner" in Green Street (2005) and "Kevin" in Sin City (2004)

How These Roles Differ from the Usual: Dark villanous roles from an actor who became famous for playing Frodo Baggins in the Lord of the Rings trilogy.
I couldn't remember Wood as a child actor when I saw him as Frodo in Lord of the Rings so he was a new face to me and probably the face that would many would ALWAYS remember him as. When people look at him, they would always remember the emo Hobbit making his way to Mordor. He's made numerous attempts to break out of this by playing a series of creepy characters. The first would be his stalker creep character in "Eternal Sunshine", the second as the cannibalistic serial killer Kevin in "Sin City", the third as a violent football hooligan in "Green Street". Maybe now he'll be typecast as "the creepy guy who used to play Frodo" but I thought he did really well in these roles. Oh, and he also did that film, "Everything is Illuminated".
1 (Click to reveal)Robin Williams as "John Keating" in Dead Poets Society (1990), "Sean Maguire" in Good Will Hunting (1997), "Finch" in Insomnia (2002), Sy Parrish in "One Hour Photo" (2002)

How These Roles Differ from the Usual: Dramatic turns and villanous portrayals from an actor normally doing comedy.
I think for every bad Robin Williams role, there's a good one. For every RV, there's a Good Will Hunting. For every Man of the Year, there's an Awakenings. I don't like most of Robin Williams' comedy roles. I liked him in Aladdin because I didn't have to see him. The only comedy movie I liked him in is Mrs. Doubtfire. And maybe Jumanji. I think most people know him as a comedian though, which is why I put him in here. He has tremendous talent when playing dramatic roles or as sociopaths. I don't know about other people who saw it, but his character in One Hour Photo scared the shit out of me. His role as the villain in the Al Pacino crime movie, Insomnia, is subtle but builds up to something intense.
Then there are his drama roles. Here's some trivia for you: whenever Williams has to do a dramatic role, he grows a beard (I don't know if this includes Jumanji heh heh). His Oscar-winning performance for Good Will Hunting will always be his tour de force performance for me, however. I can't find words to describe what that character made me feel and I really wish Robin Williams would do more dramatic roles instead of letting himself run crazy in shit like License to Wed.
Notable Instances Where I Think Playing Against Type Worked:
Tom Cruise in "Collateral", villanous performance straying from his usual good guy roles.
Mary Tyler Moore in "Ordinary People", cold distant performance from an actress known to be the motherly type.
Sean Penn in "Fast Times at Ridgemont High" (even though it's like his first role so it probably doesn't count lol)
Viggo Mortensen in "A History of Violence" and "Eastern Promises", different types of performance to move away from being typecast as Aragorn.
Eddie Murphy in "Dreamgirls", musical/dramatic performance from actor commonly known for his comedy.
Paul Giamatti in "Shoot 'Em Up", villainous performance from actor who usually does comedy.
Al Pacino in "Angels in America" and "Merchant of Venice"
Macaulay Culkin in "Party Monster", weird performance from ex-child actor (I liked it but a lot of people think it sucks!)
Michael Douglas in "Falling Down", violent and villainous performance from actor commonly known as the good guy (except Wall Street)
Where Playing Against Type Went Wrong:
Edward Norton in "Death to Smoochy".
Jim Carrey in "The Number 23".
Russell Crowe in "A Good Year".
So, discuss typecasted actors and instances where you think they tried to break out of being typecasted.