Reese Witherspoon used to be a really interesting actress. You might not know that if you judged her career solely on her post-Oscar film output, but she used to make some fairly daring choices. Yes, the seeds for her career slump were sown before she won Best Actress for her portrayal of June Carter Cash in Walk the Line (a role which, arguably, is more supporting than it is lead), but even though she tended towards some highly commercial and homogenously Hollywood fare, she was still trying to balance things out with smaller, less commercial movies and in her "teen" phase she tended towards offbeat roles rather than more typical teen fare. And then she won an Oscar and the interesting movies ceased, but the commercial success (for the most part) of her "Hollywood movies" disappeared as well.
Witherspoon's film career started strong when, at 15, she landed the lead role in the coming-of-age film The Man in the Moon, which it seems that few people have seen, but which is definitely worth seeking out because it's a pretty great little movie. She spent the remainder of her teen years acting in small roles in feature and TV films and then jumped into more adult fare with roles in films like S.F.W. and Freeway, which was well-received in general and particularly for Witherspoon's performance. She followed that up with the teen thriller Fear, in which she played a far more typical teenage Hollywood heroine than in her previous films, and then Twilight (no, not that one), in which she has a small role playing a sexually precocious runaway opposite Paul Newman. The little seen, and not particularly loved, romantic comedy Overnight Delivery followed, and then came Pleasantville, a critically acclaimed film which holds up pretty well today. In it, Witherspoon plays a stereotypically shallow high school Queen Bee who is transported along with her brother into a 1950s TV show and learns how to be a more fully formed human being. Her performance in the film displays both a level of skill which suggests her potential as an actress, and a level of charisma which suggests her potential as a movie star.
Cruel Intentions, a modern day take off on Dangerous Liaisons followed, casting Witherspoon as the virginal victim of a plot by a pair of scheming step-siblings. Although the film received mixed reviews from critics, it was financially successful and is something of a guilty pleasure movie for people who came of age during the 1990s. Her next film was Election, which was the real revelation of Witherspoon's potential as an actor. Turning her previous "teen queen" roles on their head, in Alexander Payne's film she plays a tightly-wound overachiever hell-bent on winning the class presidency. Although it's Payne's post-Election output that has been showered with awards and nominations, Election is his best film and Witherspoon's performance is one of the best he's ever captured.
The triumph of Election was followed by Best Laid Plans, a generic crime thriller, and then American Psycho, a wonderfully twisted movie about materialism and narcissism taken to its most extreme. Both Election and American Psycho are daring choices, particularly in light of the direction Witherspoon's career was heading: reigning romantic comedy queen. She transitioned pretty quickly in that direction, starring in the hits Legally Blonde, its sequel, and Sweet Home Alabama, while also balancing things out by taking roles in more high brow fare such as The Importance of Being Earnest and Vanity Fair. Walk the Line came next, assuring her ascendancy amongst Hollywood actresses... or, maybe not. Just Like Heaven was a box office hit, but received badly by critics, and was followed by a series of films which were not particularly well-received by critics and failed to find an audience, including Penelope, Rendition, How Do You Know? and This Means War. She also starred in Four Christmases, which was a hit despite being terrible, and Water for Elephants, which found an audience and was generally well-received by critics. The point is, Witherspoon's career become devoured by the "romantic comedy beast," boxing her into a very specific kind of role even while returns have made it increasingly unviable, bringing her to a sort of dead end where she's seen as being able to do this one thing, but it's a thing that no one wants to take a chance at making anymore. This isn't entirely Witherspoon's fault because, while actors can become stars in essentially every genre, actresses are rarely allowed to anchor any genre other than the romantic comedy, but, still, the interesting "little movies" that allowed her to stretch and show different facets as an actress disappeared during the last decade or so of her career, leaving nothing except those failed and middling mainstream movies to define her as an actress.
I would say that Witherspoon has rebounded slightly with a small role in this year's Mud, except that the film, though quite good, is all about men and what it means to be a man, with the female characters relegated to the sidelines, serving to help men define their manhood (or lack of it, as the case may be) but little more. She also starred in The Devil's Knot, critically savaged at its TIFF premiere and as yet unreleased. 2014 has potential for a more thorough rebound with roles in Paul Thomas Anderson's Inherent Vice and a couple of projects which sound like Oscar movies on paper, but for the time being I'm going to go with... Oscar cursed.