Adventureland (Greg Mottola, 2009) 
Adventureland is a sweet, thoughtful film about early twenty somethings dealing with that strange middle ground between being thrust into the real world and still being able to hang out all summer and smoke pot. It's about characters who are somewhat misfits, who can talk about 80s college rock and Russian literature while working in a horrible amusement park job. It's about living in the mid 80s and yet it rarely uses its nostalgia for cheap laughs or exploitation. In short, it's just about everything that most Hollywood films of its kind are not: smart, thoughtful, and tethered to some semblance of reality.
James (played with the right mix of intellectual awkwardness by Jesse Eisenburg) is a recent college graduate getting ready to head to grad school. His family's financial situation forces him to take a thankless job working at a second-rate amusement park, manning the less than honorable games booths. It's in this lost summer that he falls for Em (Kristen Stewart), another games employee who is involved in a complicate relationship with her family as well as a clandestine affair with the park's married maintenance man (Ryan Reynolds). Both Eisenburg and Stewart are superb in understated roles; they're not flashy performances, but they're rooted in a truthfulness for characters their age. Things get moving, they get complicated, they fall apart but none of it feels forced or in authentic. Mottola, who never makes the characters over dramatic archetypes, cares enough about them to make them actual humans, which many movies about people this age completely ignore.
Every performance in Adventureland makes sense, from the purely comedic supporting roles of Bill Hader and Kristen Wiig to the more nuanced and fleshed out performances of Reynolds and Martin Starr as James's nebbishy, Russian literature loving co-worker. Reynolds' character especially, though not always prominent, is an interesting figure. As a musician who's supposedly played with Lou Reed, he's an epitome of cool to the kids working at the park. As the film progresses, his actions show him to be someone completely else to the world outside Adventureland, which James begins to recognize. It's the more colorful characters surrounding the two main ones that add to the film while never taking away from the central relationship story. These characters aren't cheap 80s stereotypes and they're not there for cheap laughs. There are definite 80s "guys" and there are characters used for laughs but they're all treated with some sense of thoughtfulness for their use. It's a credit to Mottola's smart writing that everything feels integral to the story at large.
The only issue I have with the film is its use of kindred spirit characters. James occupies a world that's on the surface appears very anti-intellectual and soul-deadening but ends up finding people like himself in Em and Joel. Granted, Pittsburgh, where the film is set is a bit bigger than where I live, but its seems a little too convenient that characters like this exist for James to connect to. I happen to work in a soul-deadening job in a depressing city and I have never met anyone in my job who could tell me who Dostoevsky or the Velvet Underground where. While I recognize and sympathize with these characters, I do feel a sense of jealousy for James in that you would be able to find someone like Em at a place like Adventureland. But after all, it's still only a film.