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.
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.
Today In Madonna History 
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.
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!