Lloyd Howard (Billy Burke) is the worn-down principal of the high school in Highland Park. Although budget cuts continue to drain the school's already limited resources, he and his friends -- drama teacher Shaun (Rockmond Dunbar), guidance counselor Toni (Kimberly Elise), football coach Rory (John Carroll Lynch), bus driver Jessie (Eric Ladin), and "retired" maintenance man Ed (Danny Glover) -- do their best to inspire the students and keep the school alive with the little they've got left. At night, the whole gang hits the local bar, where Ed checks the powerball to see if the group's collective "lucky numbers" (which include 13, the date of Jessie's failed engagement, and the birthday Ed shares with Hitler) have hit the jackpot, a ten-year tradition. One night, Lloyd is quiet, finally confessing to Ed in private that their villainous mayor Shirley Paine (Parker Posey) has cut funding again, and all non-essential staff (everyone except Lloyd) is going to be fired. Then, 24 hours later, the gang watches in amazement as their powerball number comes up.
Without giving too much away, it will be obvious (or at least it seems like it's meant to be) to the viewer that there's a catch to the gang's winnings that will stand in the way of the numerous idealistic ways they line up to spend their money. The main thread involves the historic library at the center of Highland Park, which Shirley hopes to turn into a giant shopping mall, despite a hefty grant given to the city to restore it. Lloyd hates Shirley, both because she's evil, and also because she beat out his wife Sylvia (Michelle Forbes) for homecoming queen when they were in high school, so he announces to the press that she's committed to matching his $5m donation to public parks, as well as a commitment to restore the library with the grant money rather than demolishing it. Similarly, his friends spend money on themselves, buying new cars and new clothes, but they also donate to the school, bankrolling clean-up projects and paying for desperately-needed equipment.
For awhile, it appears that director / co-writer Andrew Meieran's point is that it's up to a community to instigate change, to step up and provide when the world will not. That's a reasonable message, but the film eventually undermines that idea, presenting obstacles that can't be overcome by sheer willpower. One might argue that it's not fair to hold Meieran to the rules of reality in writing a fictional film, but so much of what makes Highland Park interesting and compelling to watch is its uncompromising portrait of the struggle to get by in a dying town, where well-meaning people, particularly the young people at the school, are presented with so few options. Boarded-up storefronts are a familiar sight all over the United States, and the fact that the ones that appear in Highland Park are authentic only adds to their dramatic power. It's hard to believe, even at the halfway point, that Meieran could possibly conceive an ending that maintains the film's specific blend of tough and bittersweet, and sure enough, he's forced to retreat into convention and convenience, although he strings the film out as long as possible.
Throughout, the film is buoyed by a charming ensemble cast, which also includes character actors Blake Clark and Bob Gunton, "True Blood" star Deborah Ann Woll, and a cameo by Bo Derek. Parker Posey is kind of wasted playing Payne, a minimal role that lands firmly in her wheelhouse, but everyone else brings an authentic small town modesty to their characters, playing comic moments subtly. Lynch takes nearly irrelevant elements, like his father's memory loss, and elevates them into something kind of sweet, and Burke traces a nice arc from cynicism to idealism and back. Highland Park is not a film without a measure of charm, but it's frustrating to watch a film that so effectively captures a hard and complicated truth, only to abandon it in favor of the neat bow of film fantasy.
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