This is the 15th post in a biweekly series. Read about the series — and just what we mean by “freestyle music” — here. Freestyle Fridays post on the first and third Fridays of each month.

In the late ’70s and early ’80s, John “Jellybean” Benitez was a New York City DJ, working at Electric Circus, Hurrah, Xenon, Paradise Garage and Studio 54. In 1981, he was hired as the resident DJ at Funhouse, and he hosted a weekend dance radio show on WKTU. He started to remix songs for artists, such as—significantly—Afrika Bambaataa’s  ur-freestyle single “Planet Rock.” He also worked with Stephen Bray of the group Breakfast Club, and met Bray’s band mate, Madonna. A two-year romance developed—and pop music was changed forever.

Jellybean remixed Madonna’s self-titled debut album in 1983, clearly bringing his freestyle trappings into the different songs in varying degrees. The more obviously freestyle songs—“Burning Up,” “Everybody”—feel like raw, unpolished Madonna, the scrappy and hungry young woman from the dirty NYC streets. This street-smart, artsy period has always been part of Madonna’s creation myth; I can easily see these songs both as authentic artistic expressions from the young Madonna (and Jellybean), and as product of the canny marketing we’ve come to recognize as Madonna’s modus operandi.

Personally, I have always preferred the less freestyle songs on Madonna. I tend to think of the freestyle songs as “early, rough” songs, while the more complex songs like “Holiday” or (my personal all-time favorite Madonna song) “Borderline” seem more sophisticated, musically and lyrically. Even the videos for these songs support my interpretation: the freestyle songs have low-budget videos heavy with cheesy early 80s production, while the videos for the sophisticated songs a beautifully shot and produced, and changed what we expected from the music video genre. But if you listen carefully, “Borderline,” “Holiday,” and “Lucky Star” all carry traces of freestyle without, I think, actually being freestyle songs.

After the success of “Madonna,” Jellybean started work on his own first album, “Wotupski!?!¸” which was released in 1984.  Madonna wrote “Sidewalk Talk” for him—reportedly in two days — and provided “background” vocals. (Lead vocals are sung by singer Catherine Buchanan, though even at the time critics wondered at the “lead” and “background” vocal designation decisions.)

It’s safe to say Jellybean has helped shape pop music—and not only because of his work with Madonna. A very short list of other artists whose hit singles he remixed and/or produced: Whitney Houston, Hall & Oates, George Benson, Shalamar, David Bowie, Taylor Dayne, Patti Austin, Sheena Easton, Talking Heads, James Ingram, Billy Joel, Fleetwood Mac and Lindsey Buckingham, John Waite, The Pointer Sisters, Debbie Harry, a-ha, Michael Jackson and Paul McCartney.

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