With his comic bona fides firmly established, Guest graduated from co-writing and starring to writing, directing (and also starring!) in 1996’s Waiting For Guffman. But this time around, he set his sights on an even bigger, even broader satirical target than just dinosaur-rock obliviousness: the tragicomic, but often just plain tragic, world of community musical theatre.

The instant cult classic documents the tumultuous mounting of a musical celebrating the 150th anniversary of Blaine, Missouri, a town that’s awfully proud of itself for no discernible reason. The production is masterminded by Corky St. Clair (Guest), a frustrated would-be theatrical maestro who sees an opportunity to finally realize his big show business dreams on the smallest possible scale.

The movie ends with a performance of the musical that is a delirious symphony of blissful, unselfconscious incompetence, full of cardboard sets, hilariously wrong-headed musical numbers and performances so huge they’re pitched less to the rafters than to faraway galaxies. After a strapping young man drops out of the play, the effete and decidedly middle-aged St. Clair fills in for all of the roles he was scheduled to play, from a child to a pioneer, despite being egregiously unsuitable for the job. The climactic musical could not be more wonderfully inane yet when the Broadway bigwig of the title fails to show up for the big show, it’s surprisingly heartbreaking all the same. As This Is Spinal Tap indelibly reminded us, there’s a thin line between clever and stupid. Waiting For Guffman is an extraordinary clever look at a profoundly stupid endeavor.