"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 about 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.