In February 2010, MTV president Van Toffler announced to the world that his network was officially abandoning its ties to Generation X in favor of catering to the more socially conscious and friendly millenial generation. Toffler explained that the youth of today are much less jaded and anti-social than the slackers of MTV’s inception and heyday. This generation gap hilariously plays out in the new dark comedy, Greenberg.

Ben Stiller stars as Roger Greenberg, a 40-year-old male who was once a 1990s hipster in an up-and-coming indie rock band. Nearly 20 years later, he has become a surly, clinically depressed pain in the ass. While most of his contemporaries are raising families, Greenberg spends his time writing angry letters to large corporations, bitching about mundane details lost on the general population.

Greenberg’s arrival to Los Angeles comes when his brother takes the wife and kids on vacation to Vietnam, leaving Roger in charge of the house. That’s when he meets the family’s assistant, Florence (Greta Gerwig). She’s a shy but amiable 20-something who winds up falling for Greenberg, despite his myriad personality flaws and poor treatment of her.

Greenberg is the latest collaboration between director Noah Baumbach (Margot at the Wedding) and his wife, actor-producer Jennifer Jason Leigh. The two teamed with Academy Award-winning producer Scott Rudin several years ago to bring Greenberg – a love letter to Los Angeles – to the big screen. Baumbach and Leigh conceptualized the story and shot many of its scenes at notable places such as the Silver Lake Lounge and the world-famous Sunset Strip.

“Since I grew up in Los Angeles, I see the city in a very personal way, and I wanted to show Los Angeles the way I grew up in it,” explains Leigh. “There’s a light in L.A. that is very different from the East Coast, and there’s an expansiveness. There is much that is ugly in L.A., but also a kind of beauty in the ugliness. I love that there are still sections of the Sunset Strip without high-rises. That you can be at a farmers’ market surrounded by 1920s Craftsman homes and then halfway down the street is a 99 Cents store. The way the dust catches the light, how green it is, the beauty of the sky in winter.”

Stiller was instantly drawn to the material after seeing several of Baumbach’s other projects. When approached by the husband-wife duo, the actor-comedian jumped at the chance to work with them both.

“I was a fan of The Squid and the Whale – the reality, the tone and the emotion of it – and Margot at the Wedding and Kicking and Screaming,” says Stiller. “Noah finds the humor without going for laughs. So I was very excited to get this script and then get to talk to him about it. When we got into the process of working on the movie, I knew I was with a filmmaker who had a really clear vision of what he wanted to do and a point of view – yet was also open to what’s going on in the moment.”

As for the generation gap, that’s a truly exciting thread woven throughout the film. Much ado was made in the pre-millenial years about Generation X. Now that everyone from that demographic has turned 30-something (and in some cases, 40-something), it’s the next generation calling the shots.

In a surprisingly heartfelt and hilarious party scene, Stiller as Greenberg points out – with amazing clarity – the differences between himself and a group of college students with whom he’s been partying. In doing so, he has an epiphany about his own shortcomings as an adult, with a particular focus on his relationship with Florence. In the end, according to Baumbach, it’s what takes this comedy to the next level.

“Florence is willing to put up with a lot if she believes in somebody, and she sees something in Greenberg – a sweetness, a vulnerability. And she’s right. In the end, she’s rewarded for sticking with him. And Greenberg is able to get out of his own way for a moment. That they can find this grace moment is a big deal for both of them.”

Greenberg is currently in theaters.