One man's fight to free his brother from a rough estate leads to a tournament to secure the new leader of the estate.

Sexy. Style-conscious. Extreme love affairs. Complicated friendships. Life happens all too quickly when Cloey is reluctantly plucked from her comfort zone and complete reliance on others is overturned – a secure relationship with her boyfriend unravels, her childhood best friend is moving away and daddy’s (Daniel Baldwin) checkbook closes. City Baby comments on the ladder-climbing mentality of always reaching for the next bigger, better thing – relationship, city, job – when sometimes what's right in front of us is just fine. Scattered with cameos from Portland musicians like Stephen Malkmus of Pavement, live musical performances by Glass Candy and Starfucker, and a thoughtful soundtrack featuring all Portland bands and musicians, City Baby depicts a playground for semi-adults, revolving through the lives of cool kids.