Today in Madonna History: December 16, 1989


On December 16 1989, Dear Jessie debuted at #9 on the UK Singles Chart.

The single would climb to its peak position of #5 on December 30th, where it remained for three weeks before beginning its descent.

2 responses

  1. This song should’ve been released after Cherish like in September 1989 in the Usa, and then Oh Father which did hit the Top 20. I love the jazzed up single version of Dear Jessie. However, stupid warner should have made a video for Keep It Together her 6th single. I wish Love Song was released as it would’ve hit top 3. Every Like a Prayer song would’ve hit big except Act of Contrition.

  2. Dear Jessie is a wonderful Madonna song-it crosses paths with the following Madonna songs-Secret from Bedtime Stories, Little Star from Ray of Light, What It Feels Like for a Girl from Music and Dark Ballet from Madame X!

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