|Ben Kingsley||Dr. Squires|
|Josh Peck||Luke Shapiro|
|Famke Janssen||Kristin Squires|
|Talia Balsam||Luke's Mother|
|David Wohl||Luke's Father|
|Bob Dishy||Grandpa Shapiro|
|Joanna Merlin||Grandma Shapiro|
It's summer in New York City, the year is 1994, and teenage marijuana dealer Luke Shapiro is trading dime bags for sessions with his therapist, Dr. Squires . Luke has girl troubles and self-esteem issues, but the doctor has problems of his own -- namely, his deteriorating marriage and midlife crisis. Together, the mismatched pair launch across the metropolis on an odyssey full of girls, hip-hop and cannabis smoke.