The Black Rider is probably the most challenging Tom Waits album, which makes it either the worst or best entry point into his vast catalog, depending on your point of view. The fruits of a collaboration with William Burroughs and director Robert Wilson, The Black Rider is a play based on the German folktale Der Freischut, and the resulting soundtrack unfortunately fails to cohere into anything resembling an album. Listening to these songs of deranged calliope melodies, haunted ballroom music, ghostly gondola serenades, swashbuckling Dixieland, and Eastern Bloc tango divorced from their context, you might guess that the stage version of The Black Rider was actually just a local madhouse’s production of Fiddler On The Roof. For nearly an hour, Waits barks about freakshows, affects a Sigmund Freud accent, and offers his phone number (beating rapper Mike Jones to this gimmick by over a decade) while the music skids recklessly between sounding genuinely compelling and sounding like someone bootlegged the Pirates of the Caribbean ride at Disney World. Rivaled only by One From the Heart (though for entirely different reasons), The Black Rider is the Tom Waits album most likely to provoke a “what the hell are you listening to?” query from anyone within earshot, and might be one of the strangest albums you will ever hear.