Dear Jessie

"Dear Jessie"
Sepia-toned image of Madonna sitting on a bed, holding the bedsheet to her bosom. She wears a Minnie Mouse headdress with a large bow. Madonna looks upwards where the word "Madonna" has been printed in uppercase letters. A hand-drawn pink elephant is squeezed inside the letter O, beneath which "Dear Jessie" has been printed (also in uppercase) with spaces between each of the letters.
Single by Madonna
from the album Like a Prayer
B-side"Till Death Do Us Part"
ReleasedDecember 4, 1989
Recorded1988
StudioJohnny Yuma (Burbank, California)
Genre
Length4:20
Label
Songwriter(s)
Producer(s)
  • Madonna
  • Patrick Leonard
Madonna singles chronology
"Oh Father"
(1989)
"Dear Jessie"
(1989)
"Keep It Together"
(1990)
Music video
"Dear Jessie" on YouTube

"Dear Jessie" is a song by American singer Madonna from her fourth studio album Like a Prayer (1989). It was released as the fifth single from the album on December 4, 1989, by Sire Records. Written and produced by Madonna and Patrick Leonard, the song was inspired by Leonard's daughter Jessie. The release of "Dear Jessie" was limited to the United Kingdom, certain other European countries, Australia and Japan. The track is composed more like a children's lullaby rather than a pop song, and features strings, synthesizer and strummed acoustics. A change in tempo occurs during the breakdown, where instrumentation from trumpets is included. Lyrically, the song evokes a psychedelic fantasy landscape, in which pink elephants roam with dancing moons and mermaids.

Upon its release, "Dear Jessie" received mixed reviews from critics, who felt that the fantasy imagery of the song was overdone, but complimented its composition. Other reviewers likened the song to the music of the Beatles. The track was a moderate success commercially, reaching the top 5 in the United Kingdom and Ireland and the top 20 in Germany, Spain and Switzerland. The music video of "Dear Jessie" combines live action and animation, portraying a young girl waking up in bed and interacting with fantasy characters. Madonna appears in the video only as an animated, Tinker Bell-type fairy.