Cameron Crowe used to be kind of a cool filmmaker. Maybe never cutting edge, exactly, but "edgy" by the standards of American mainstream films. He was never a very prolific filmmaker (save in 2011, when he released two documentaries and a feature film), averaging about three movies a decade since his screenwriting debut in 1982, but most of the films that he made had a certain cachet either as cult classics or genuine classic classics. Then he was embraced by the Academy with an extremely Oscar friendly movie, following it up with another Oscar friendly movie which would net him the prize for Original Screenplay. He was sort of an "everyman" filmmaker whose work was filled with warmth and focused on character. And then he made a film which is pretty much the exact opposite of all that came before - a dark, mind-bender type thriller that ultimately polarized critics, followed by a less than successful return to warmth. Whatever Crowe had leading up to his Oscar win, he seemed to lose after taking home the prize.
Crowe got his pop culture start as a writer for Rolling Stone and transitioned to screenwriting with 1982's Fast Times at Ridgemont High, which he adapted from his own book "Fast Times At Ridgemont High: A True Story." Although the film was not particularly well received by critics at the time, it has gone on to become considered as one of the best "high school" movies ever made, notable for its frankness and for featuring what is, perhaps, Sean Penn's oddest (and I mean that in the best way) performance. He followed up with the screenplay for The Wild Life, another story about Los Angeles teenagers, albeit one that has never attained the level of his previous effort, perhaps due to the fact that issues regarding music rights have kept it from being released on DVD. He closed out the 1980s by transitioning to the director's chair, making one of his best films, Say Anything.... A well-received film which has managed to maintain its status as a great film about teenagers, due in part to the iconic image of its hero standing outside his love interest's window with a boom box, it's one of the defining films of its time and of its genre.
Depending on your perspective, Crowe started the 1990s as strongly as he ended the 1980s. In my own experience, there are two types of film viewers: those with an abiding affection for 1992's Singles, and those who have never seen Singles. A romantic comedy set against the backdrop of the Seattle grunge scene, Singles is arguably Crowe's most mature film and spawned numerous imitators, including the more well-known Reality Bites. Up through this point, Crowe was something of an acquired taste, a director and screenwriter whose work was beloved by a segment of the filmgoing public without ever being universally embraced. His next film would change that, his next film being the massively successful, massively mainstream Jerry Maguire. The film would be nominated for 5 Oscars (including Original Screenplay for Crowe) and, ironically given the relatively small profile of his previous efforts, was the sole "big studio" picture to be nominated in the season which became popularly known as "The Year of the Independents." Crowe was now firmly established and his follow-up would only seem to affirm his status as a maker of solid, unthreatening films. Almost Famous, a film beloved by many (myself included), was not financially successful it its theatrical run, but was well-received by critics and gained 4 Oscar nominations. It would win in the category of Best Original Screenplay, which seemed not only like a just reward for the film itself, but an acknowledgement of Crowe's solid work as a screenwriter for going on two decades. Ideally, things only would have gone up from there. But instead...
First up was a reunion with Jerry Maguire star Tom Cruise in Vanilla Sky, a science fiction mystery thriller. It is, as I said, the opposite to the type of movies Crowe had made previously, which shows in its somewhat "over directed" style, a sharp contrast to the more relaxed nature of his previous directorial efforts. The film was a commercial success, but had a mixed critical reception, particularly in comparison to Open Your Eyes, the Spanish language film on which it is based. Next came Elizabethtown, a return to form in attitude, if not in artistry. A critical and commercial disappointment, the film would go on to inspire Nathan Rabin's Flops series (I suggest not clicking that link unless you have a couple of days to read through the entirety of the compulsively readable series). It, and its follow up We Bought A Zoo are films which know the steps of a Cameron Crowe film, but lack the rhythm of one. Sentimentality isn't necessarily a bad thing - Almost Famous drips with it, after all - but it requires some sharp character work in order to keep from being cloying, and that's what Crowe's more recent efforts have lacked.
So what happened to Cameron Crowe? Why is it that after winning an Oscar his work crossed over the line from workably sentimental to unforgiveably mushy? The answer is clear: Oscar cursed!