From dark dream sequences to Christopher’s comatose glimpse of hell and Paulie’s eerie vision of the Virgin Mary on the Bada Bing stage, The Sopranos repeatedly invoked the uncanny and the supernatural. So it’s no surprise that show also featured two prominent references to one of the greatest spook tales of all time, Washington Irving’s “The Legend of Sleepy Hollow.”
The first occurs in “Cold Cuts” (Season 5, Episode 10). On the drive upstate to Uncle Pat’s farm in Kinderhook (to exhume some murder victims from their graves), Tony Blundetto randomly admits to Christopher that “some very sorry people” (presumably kids who suffered for insulting him) used to call him Ichabod Crane. The line then gets a callback in a later scene in the episode. Tony Soprano joins his cousin Tony in ribbing Christopher and mocking his beak nose as they all eat dinner together, until the aggravated Christopher finally snaps at the relentlessly joking Blundetto, “You know I could have called you Ichabod Crane, but I didn’t!” A petulant retort, for sure, but also a pretty funny one, because if ever there was someone who could be cast as Ichabod, it’s Steve Buscemi’s Blundetto.
The second reference is in “Luxury Lounge” (Season 6, Episode 7). Phil Leotardo passes along to Tony Soprano Johnny Sack’s appreciation for his taking out Rusty Millio, but Tony acts coy and claims to have had nothing to do with the hit. Phil laughs off Tony’s cautiousness, and says, “Anyway, Rusty’s gone, and we’ll chalk it up to the Headless Horseman.” A strange name drop, although it does make geographic sense that a New York crime boss would reference Sleepy Hollow’s favorite specter. Phil’s line also has some sinister resonance, considering that Rusty was dispatched by a shot to the head (an assault of brain-scrambling impact, akin to a Horseman gourd toss).
More than just another mob story, The Sopranos was a pop cultural phenomenon. How apropos, then, that the series referenced a pair of legendary Irving characters that have been imprinted on American consciousness for over two centuries now.