Synopsis

Semisonic's performance is intercut with a romantic mixtape story. A young man carefully assembles and sends a cassette to a woman he hopes to reach through music. As she listens, the songs become a private emotional connection, while the band performs in a stark studio setting. The video's central joke is recursive: the cassette's handwritten track list includes "Singing in My Sleep" itself, turning the band's song about the power of mixtapes into part of the imagined mixtape.

Factoids & Trivia

• Semisonic invited fans from its email list to help create an "Ultimate Mix Tape" for the video. Fans could suggest songs and contribute artwork for the cassette insert. Participants received personalized thank-you gifts, while the winning contributor received a copy of the finished video.

• The handwritten track list shown in the video reportedly includes songs by Blondie, Elvis Presley, R.E.M., Radiohead, Trip Shakespeare, and Semisonic.

• The video reflects the song's central idea that a carefully chosen collection of songs can function as an intimate romantic message. Its use of a cassette also captures the late-1990s mixtape culture that the lyrics celebrate.

• Dan Wilson said the song was inspired by receiving an especially effective mixtape. The word "Sony" came from the logo visible on the cassette as it played, while "Did you ever look so nice" was taken from the title of one of the songs on the tape.

• "Singing in My Sleep" was released as the second single from *Feeling Strangely Fine* on August 18, 1998.

• During live performances of the song, drummer Jacob Slichter could play the keyboard part with his right hand while continuing to play drums.