In a small beachfront town in Florida, rival developers are vying to try to buy up all the property from those who've lived there for years. Returning home for the first time since she was 15 is infomercial actress Desiree (Angela Bassett), who is hoping to make peace with her stern mother, Eunice (Mary Alice). Eunice has taken under her wing her late nephew's son Terrell (Alexander Lewis), but hasn't managed to steer him clear of trouble: As the movie opens, he's setting fire to a float scheduled for use on Buccaneer Day, an attempt at creating a tradition-based local holiday by chamber of commerce booster Francine (Mary Steenburgen, terrifyingly convincing).
The developers are vying for land currently occupied by a motel-restaurant combo run by once-aspiring actress Marly Temple (Edie Falco, Oscar-worthy in the best female performance of the year so far). Marly's dad (Ralph Waite) is aggressively opposed to selling, even as he bemoans new laws that constrain businesses.
The main story lines followed are those of Desiree and Marly, who only cross paths directly once, early on, though the other people in their lives are mostly shared in some fashion. Driven out of town at a young age by her mother, Desiree now has to come to grips with her mother's resentment that she hasn't spoken to her in so long. Marly is in some ways the opposite: She aspired to bigger things that would've taken her out of town, but instead wound up running the family business because it's what her father wanted. Both must deal with the adjusted expectations of leaving youth behind and decide to what extent they're going to accept or deny the past.
The past -- the nation's, the town's, the individual characters' -- is part of the film's larger theme. One older black man is nostalgic for segregation; Francine's busy trying to create a tradition out of the state's immigrant history, but is stymied by the unfortunate truths of historical genocide and slavery; and Terrell's a good kid with a dangerously delinquent side inherited from his father. Then, of course, there's the whole past-versus-future dynamic of "redevelopment."
Lest this all sound too much like civics class, however, rest assured there's plenty of dry humor. Sayles seems almost as amused by contemporary tackiness as he is righteously appalled by some of its effects, and that fine line gives the movie's final joke its punch.