In a loose parody of Sam Raimi's Drag Me to Hell, a young businessman (Samberg) is cursed by a homeless shaman (Fred Armisen) to be haunted by a sexy, shirtless saxophonist named Sergio (played by host Jon Hamm) after stepping on the shaman's dreamcatcher and not paying for it.

The saxophonist is loosely based on a scene from the 1987 film The Lost Boys featuring musician Timmy Cappello.

The Lonely Island celebrate their 100th Digital Short by revisiting many digital short favorite characters (Shy Ronnie, Dennis the Drug Addict, Michelle the Body Fuzion Lady, The "Dick in a Box" singers, etc.), clips from previous Digital Shorts, and fresh footage from numerous celebrities.