"Sidewalk Talk" is a song by American record producer John "Jellybean" Benitez from his first extended play, Wotupski!?! (1984). It was released on October 21, 1984, by EMI Records as the first single from the EP. The song was written by Madonna and produced by Benitez. They had initially met in 1983 and Benitez worked as a producer on some of Madonna's self-titled debut album. When he started work on his debut EP, Wotupski!?!, Madonna wrote "Sidewalk Talk" for him. The song features bass and electric guitars, synthesizers, piano as well drums. Lead vocals are sung by Catherine Buchanan, and background vocals by Madonna.

"Sidewalk Talk" received mixed reviews from critics, with David Nick Ybarra questioning crediting Buchanan as lead vocalist, instead of a better known singer like Madonna. The song was released initially in 12-inch promotional CD in remix formats to the DJs and the clubs, and reached the top of the Billboard Hot Dance Club Songs chart. It was later released commercially in 7-inch and 12-inch formats, and charted on the Billboard Hot 100. The song also had minor chart placements in the Netherlands, New Zealand as well as the United Kingdom.

In 1983, Madonna met John "Jellybean" Benitez, who worked as a DJ at the Funhouse club in lower Manhattan. Soon after, they started dating each other and worked on Madonna's self-titled debut album, released in 1983. When Benitez started work on his debut EP, Wotupski!?!, he asked Madonna to write a song for him. Within two days Madonna wrote "Sidewalk Talk", whose idea she had initially thought of using on her debut album. According to Benitez, Wotupski!?! was a concept album, "It's a street slang in the Bronx. It means 'what's up, what's new'?" The artist credit of the song was simply Jellybean, with lead vocals credited to Catherine Buchanan. Madonna provided background vocals for the track with Audrey Wheeler and Cindy Mizelle. Benitez produced the track as well as arranged and mixed it. Michael Hutchinson assisted on engineering, recording and mixing the track. Producer Stephen Bray also arranged "Sidewalk Talk" with Benitez. Instrumentation featured in the track included bass guitar by Marcus Miller, synthesizer by Boyd Jarvis, Fred Zarr and Bray, electric guitar by Ira Siegel, percussion by Bashiri Johnson and Trevor Gale, and lastly drum programming by Benitez and Bray.

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