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's 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). Francine is married to Earl (Gordon Clapp), a compulsive gambler who occasionally ineptly attempts suicide and is in league with one of the developers, the strategy-minded Lester (Miguel Ferrer), who uses terms like "beachhead" and "hostile natives." On the other side is Jack (Timothy Hutton), a landscaper who likes to keep certain trees and landmarks intact in the interest of making people feel like they're in nature, only with more control ("Nature on a leash," as another character puts it). Both Jack and Lester are vying for land 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. And Marly's mom is a school drama teacher who once taught Desiree and now recruits Terrell to build stage props as part of his community-service arrangement. And we haven't yet mentioned the local football hero with an embarrassing secret or two, or the aging golfers whose segments serve as the wraparound for the entire story.
The main plotlines followed are those of Desiree and Marly, who cross paths directly only 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. When Desiree laments, "I don't like who I am down here," she speaks for all of us who like to think we've changed and yet find ourselves regressing when we return to the realm of our childhoods. 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, noting that back then some black people actually owned a few of the local businesses, because no white men would set up shop in their area. Francine is 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. Terrell is a good kid with a dangerously delinquent side inherited from his father; can he go right, or is he similarly doomed? And 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. One character is introduced, out of the blue, in extreme close-up, and as he rambles on about what things were like in his day, the camera slowly pulls back until it ultimately reveals a sly joke so obvious that you won't expect it. A laconic alligator wrangler seems directly cribbed from the documentary Home Movie. There's even a possible nod to Quentin Tarantino, as Sayles throws in a conversation about an old TV show that's as hilarious as it is pointed. 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.