Critical reception Ī review of "Singing in My Sleep" in the issue of Billboard said the song's intro is "a shapeship-like whir and a funny, plinking melody", but that ultimately, the track is "pure, mass-consumption pop." In a review of the maxi-single, Michael Frey of Allmusic called it "a melodic ode to the art of making mix tapes". In exchange, those fans received a personalized "thank you" token from the band, while the winner was also sent a copy of the video clip. The band invited fans from its e-mail list to participate in a song swap in which fans could help choose songs for an "Ultimate Mix Tape," to be used in the "Singing in My Sleep" video. The music video for "Singing in My Sleep" was directed by Chris Applebaum, who helmed the video for Semisonic's previous single, " Closing Time".
This was one of the Semisonic songs for which band member Jacob Slichter played the keyboard parts with his right hand while playing drums simultaneously. Wilson said the lyrics came easily once he allowed himself to use these phrases. Another lyric, "Did you ever look so nice", was the name of one of the songs that had been included on the mixtape.
A way to seduce someone is to make them a list of music, a playlist that, once they hear, they’re more likely to fall in love with you." He incorporated the word " Sony" into the song's lyrics because the company logo was visible at the center of the mixtape as he watched it going around in his cassette player. Club, Dan Wilson recalled how the idea for the song came about: "Someone that I knew had sent me an amazing mixtape, and I was loving every song.