"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 10, 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 complained about the overdone fantasy imagery of the song, but complimented its composition. Other reviewers likened the composition and performance to the style of The Beatles. The track was a moderate success commercially, reaching the top 10 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 little girl waking up in bed and interacting with fantasy characters. Madonna appears in the video only as an animated, Tinker Bell-type fairy.

When Madonna started work on her fourth studio album, Like a Prayer, she was in an emotional state of mind following her divorce from Sean Penn, her 30th birthday and unfavorable reviews for her acting endeavors. She had certain personal matters on her mind that she thought could be the musical direction of the album. As Madonna considered her alternatives, producers Patrick Leonard and Stephen Bray experimented with instrumental tracks and musical ideas for her consideration. One day, while recording of the title track was going on at Jonny Yuma Studios, producer Patrick Leonard had to pick up his daughter Jessie from school and, since his wife was out of town, had to bring her back to the studio. Madonna, who was initially angry with Leonard for his late arrival, struck up a rapport with Jessie. She commented: "It was like as if I was my mother and [she] was me. We were playing in our backyard again." Witnessing their connection, Leonard approached Madonna with a song he had written for his daughter, titled "Dear Jessie". Madonna changed some of the lyrics and agreed to record the track for Like a Prayer; it was finished within the next three days.

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