On February 2 1985, Sidewalk Talk peaked at #1 on the Billboard Hot Dance/Club Play chart. The song was written by Madonna, who also contributed vocals on the chorus and bridge while the verses were performed by Catherine Buchanan. Madonna gifted the song to producer/remixer/DJ/boyfriend Jellybean Benitez for use on his debut EP, Wotupskii!!?! and it was promoted to clubs by EMI Records in October, 1984. It was eventually issued as a commercial single, climbing to #18 on the Billboard Hot 100.
Sidewalk Talk was arranged by Stephen Bray & Benitez with vocal arrangement by Madonna, according to the album’s liner notes. Madonna’s lyrics to the song recall her early years in New York and some of the challenges she encountered adjusting to big city life.