Josh Peck and Olivia Thirlby by JoJo Whilden/Occupant Films/Sony Pictures Josh Peck and Olivia Thirlby by JoJo Whilden/Occupant Films/Sony Pictures

With The Wackness, writer/director Jonathan Levine has emerged as one of the first, few voices of that generation sandwiched between X and Y: The one that had Biggie and De La, Tribe and the Wu as its own soundtrack. Set in the throbbing, sultry New York summer of 1994, The Wackness not only explores the coming of age of its characters, but also that of the culture, as New York adjusted to Mayor Giuliani and a new brand of hip-hop hit the streets.

In the intertwining stories of high-school grad Luke Shapiro (Josh Peck) and Dr. Squires (Sir Ben Kingsley), Luke's middle-aged therapist, Levine captures the simultaneous anxiety, hope, disappointment and happiness that adult life foists on us again and again. Lacking both friends and family support, Luke seeks out Squires for therapy and advice on how to get his dream girl, Stephanie (Olivia Thirlby), while spending the rest of his summer days dealing pot out of an Italian ice cart. Squires — who's also Stephanie's step-dad — has some growing of his own to do, as he considers his passionless marriage and riskless existence.

One of the many unique aspects of The Wackness is the diverse cast that mixes a legend like Sir Kingsley with newcomers like Thirlby and Peck (plus Mary-Kate Olsen in the supporting role of a local Dead-head/pot buyer). Peck, who's best known to tween audiences as one-half of the Nickelodeon show, Drake & Josh, has rarely been seen tackling subjects like drug sales and sexual pursuit. The actor said that taking the role was a "leap of faith," but he took it because he "identified with [Luke's] weakness." Peck explained, "I always felt that I had this type of performance in me, and it's something that I wanted to exhibit."

In the movie, however, Peck exhibits more than just a "performance": All the awkwardness of romantic exploration comes to the screen, including nude fumbling. "Olivia and I have been naked in front of each other and we're friends, so it adds a whole layer to the relationship," he said, adding with a laugh, "and it makes fantasizing much easier." Peck didn't take any chances with the scene in question: He skipped lunch the day of the shoot to prevent bloating.

For Kingsley, the role of Dr. Squires was similarly attractive because of the character's vulnerability. "I think that journey of vulnerability," he said, "and his childishness, there's something in him that has not matured. He needs Luke to help him mature, just as much as Luke thinks he needs my character to mature." Luckily, though, Kingsley was mature enough (and tasteful) in real life to accept a '90s-style mixtape from Levine.

Yet, with all the male maturity issues that tend to get worked out again and again in Hollywood, where does this leave the film's central female character, Stephanie? Thirlby, who's best known for her supporting role in Juno,  said that when she read the script, Stephanie "seemed like a girl who was a stereotype but wasn't really defined by that." Thirlby continued, "She's the heartbreaker, she's the hot girl, she's the popular girl. [Yet] she was something much deeper than that. Especially as a teenage girl, you can be those things, but everybody is deeper than that."

The sensitivity that Peck and Thirlby bring to their roles shines through in the finished product. Rarely do teens come across on screen like the real thing, but The Wackness' specialness is derived in part from its tender, careful portrayal — awkwardness and all. Ultimately, the meshing of generations (not to mention the rapper's delight of a supporting actor in Wu Tang's Method Man) was an illustration of the director's own fears. The bi-generational stories, Levine mused, came from "realizing that you have to continually come of age, no matter how old you get."

The Wackness opens in L.A. and New York July 3.