The Chipmunks and Chipettes participate in school journalism and end up covering the story of "Sleeping Beauty." During the investigation, Brittany pricks her finger on the spinning wheel and becomes cursed, just like the real story. They discover that for Brittany to awaken, she must receive a kiss from her 'dream prince'. The group goes on, assuming this person is Bart, later proven wrong. Afterwards, it is revealed that Alvin is this dream prince, that is, after sharing his first kiss with Brittany.
- "Wake Up Little Susie" originally performed by the Everly Brothers.
- The title is a pun on the short story The Legend of Sleepy Hollow and also spoofs Sleeping Beauty.
- The villain Maleficent is mentioned.
- This is the only episode where Alvin and Brittany share an on-screen kiss.
- This episode proves that Alvin would do anything for fame.
- Brittany doesn't believe in curses.