Between her best friend moving to Brooklyn, pressure to find employment from her pop (Daniel Baldwin), and juggling romances with an aging rocker boyfriend and a yuppie fling - Cloey is reluctantly plucked from her party girl reality to deal with her own set of common people dilemmas and accomplishments. Scattered with cameos from musicians like Stephen Malkmus (Pavement), live performances by Glass Candy and Starfucker and a soundtrack featuring all local bands, 'City Baby' documents the youth utopia of Portland Oregon, revolving through the lives of a few sexy, style-conscious kids surviving extreme love affairs and complicated friendships.

Claire Paxton is a rebellious and independent late teen, her outlook on life which is driven largely by the fact that her single mother is a self absorbed alcoholic. Claire is repeating some of her senior year classes at Toronto's Arthur Meighen High School in order to graduate, which she decides to do during the school year rather than waste her precious summer doing it in summer school. She has little motivation to attend classes or graduate. Her school year is affected largely by her encounters with two males with who she ends up spending much of her time. The first is Jim, the thirty-something front man for the funk band, the ElastoCitizens, with who she embarks on a sexual relationship. The second is Henry, a ninth grade student who she used to babysit. Henry is an exceptional student, but is at a stage in his life where he too is starting quietly to rebel against his straight-laced upbringing. Claire acts as his mentor in his coming of age, which may change if she knew that ...