Tucked underneath the sleeve of a prison jumpsuit worn by Alan (Grant Rosenmeyer) at the start of “Chasing the Blues,” you can see a tattoo of a 45 rpm adapter, the insert one would put in the middle of a record to make it playable on a turntable, on his forearm that lets you know that as soon as he sheds the jail garb he’ll go back to growing his vinyl collection. While it comes as no surprise to learn that his 20-year stretch in Taylorville, Illinois has been a result of this obsession, writer/director Scott Smith slyly doesn’t immediately let the audience know just why that is, but the day that he’s getting out is coming sooner than later as he’s approached by a dapper Southern lawyer (Jon Lovitz) who informs him that a climate-controlled storage unit full of records belonging to the late Roy Walker in Louisiana has gone unclaimed. Needless to say, once Alan is set free, he’s headed south.
Alan wouldn’t have ever gone to prison if he was as crafty as Smith in plotting the charming caper comedy he finds himself a part of, but he’s someone worth following nonetheless as he makes the trip to Plaquemine, confiding in a stranger on the bus (Chelsea Tavares) his tale of woe. As the two travel through small towns, Alan recounts not only his history, but that of Jimmy Cain Baldwin’s “O Death, Where is Thy Sting?” an album so scarce he figured it was an urban legend until he found it in the living room of Walker’s mother in Hyde Park (Anna Maria Horsford) planning to give away her husband’s collection. Unfortunately, he wasn’t the only one in pursuit of the rare recording with Paul (Ronald L. Conner), a local record shop owner, also hot in pursuit, and the two became locked in long chats over sweet tea with the lady attempting to pry the record away during an excruciatingly hot four days in Chicago.
You needn’t be a record collector or know one to enjoy “Chasing the Blues,” but Smith and co-writer Kevin Guilfoile impress with the intimate knowledge of this world, cleverly intertwining the backstory of the object of desire, complete with rumors of the supernatural as part of its lore, to explain the behavior it inspires, pushing Alan and Paul to lengths that neither would think they were capable of. Although the film mines big laughs from the rivals’ single-mindedness, it wisely resists ever becoming full-fledged wacky, as Paul, under an unfortunate late ‘80s perm, constantly proves himself to be a smart and worthy foil for Alan, who appears as bedeviled by what personal principles he’s willing to violate to get his hands on the prized 45 as he is by his fellow collector. Smith even sneaks in a subtle yet astute rumination on cultural appropriation amidst the mad dash to possess “O Death, Where is Thy Sting?” that gives “Chasing the Blues” a little extra panache.
Nicole Hirsch Whitaker’s subdued yet carefully considered cinematography and The Bones of JR Jones’ contemporary reworking of 1930s blues for the film’s score lend additional depth to a comedy that constantly rises above what appears as first to be a thin premise. Although there is some minor strain shown in Alan and Paul’s battle to outlast the other in coming up with credible reasons to keep them coming back to Mrs. Walker’s place for hours at a time, Smith keeps the energy high and unspools a series of surprises that are supremely satisfying because of how well he’s laid the groundwork for them. While hope should be held out that “Chasing the Blues” isn’t as hard to find after its premiere at the Chicago Film Festival as a copy of Jimmy Cain Baldwin’s sole album, it’s the kind of gem that’s well worth seeking out.