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.

Shy Ronnie (Samberg) and Clyde (Rihanna) team up for a second time to rob a bank. Unfortunately, Ronnie's social awkwardness puts the heist in jeopardy and forces Clyde to do most of the work.

The Lonely Island celebrate their 100th Digital Short by revisiting many digital short favorite characters, clips from previous Digital Shorts, and fresh footage from numerous celebrities.