Dear Jessie

1989 single by Madonna

This article is about the song by Madonna. For the song by Rollergirl, see Dear Jessie (Rollergirl song). For the 1998 documentary film, see Dear Jesse.

"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.

Background

When Madonna started work on her fourth studio album, Like a Prayer in 1988, she was in an emotional state of mind following her split from Sean Penn, her 30th birthday and unfavorable reviews for her acting endeavors.[1] She had certain personal matters on her mind that she thought could be the musical direction of the album.[2] As Madonna considered her alternatives, producers Patrick Leonard and Stephen Bray experimented with instrumental tracks and musical ideas for her consideration.[2]

One day, while recording of the title track was going on at Johnny Yuma Studios, Leonard went to pick up his daughter Jessie from school. Since his wife was out of town, he brought Jessie to the studio.[3] 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."[3] 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.[3]

"Dear Jessie” was released as the fourth single from Like a Prayer in Europe, while it served as the fifth single from the album in Australia and Japan; it was never released in the United States.[4] The single cover used a photo from 1987, taken by Herb Ritts.[5] It showed Madonna in bed, clutching a bed sheet to her bosom and sporting a pair of Minnie Mouse ears. The photo was a reference to the early criticism of Madonna’s work, when reviewers had described her voice as "Minnie Mouse on helium”.[3]

Composition

According to Rikky Rooksby, author of The Complete Guide to the Music of Madonna, "Dear Jessie” sounds more like a children’s lullaby than a pop song.[4] A baroque pop and psychedelic pop song,[6][7][8] it begins with the sound of strings, ushering a joyous melody, with Madonna singing in a full voice. The verses are sung without any background vocals to accompany Madonna’s voice. However, in the chorus, when she sings the lines, "Pink elephants and lemonades, Dear Jessie hear the laughter raining on your love-parade”, a different set of vocals are interwoven with hers, continuously chanting the words "La-la”.[4] Synthesizer and strummed acoustics are added during the second verse, followed by the repetition of the chorus, when a change in tempo and time signature occurs, followed by the sound of a child’s laughter.[4]

As Madonna finishes singing the intermediate lines, "Close your eyes, sleepy-head, It is time for your bed, Never forget what I said, Hang on...”, a trumpet starts playing alongside the main rhythm. The breakdown has the feel of Spanish music, with the glissando evoking the string arrangements.[4] This is followed by the bridge and the chorus being repeated twice. "Dear Jessie” ends with all instrumentation and vocals fading out, except the orchestra, which is equalized to make it sound very thin and trebly, as if coming out from a distorted radio.[4] The lyrics encourage the young girl Jessie to use her imagination. It summons up a psychedelic landscape, where pink elephants roam with dancing moons and mermaids. It references fairy-tale characters and creates an image of children playing with each other.[9]

According to the sheet music published by Warner/Chappell Music, "Dear Jessie” is written in the time signature of common time, with a tempo of 120 beats per minute. Normally written in 4⁄4, the song has a change in time signature after the second chorus, changing it to 3⁄4.[10] It is composed in the key of D major, with Madonna’s voice ranging from C3 to D5. The song’s chord progression follows a sequence of Bm–A–Bm–D–A in the verses and changes to D–Bm–G–A–D in the chorus.[10]

Critical reception

Author Santiago Fouz-Hernández commented in his book Madonna’s Drowned Worlds that to him the song felt like a trepiditation of Madonna’s thoughts about what might be termed "girlhood” and on a broadscale, on "feminity”.[11] Christopher P. Andersen, author of Madonna: Unauthorized, described "Dear Jessie” as "a wistfully psychedelic confection of carousels and pink elephants”, adding that "the song harkens back to the lullabies your mother must have sang to you”.[12] Robin Anne Reid, author of Women in Science Fiction and Fantasy: Overviews, complimented the fact that "although the sort of fantasies that [Madonna] conjures might trend towards the kinky and sexual, she can also delve into a world of mermaids, fountains of youth, leprechauns and magic lanterns as is evident by ’Dear Jessie’."[13]

her doll. A fairy goes around tapping all her toys on the floor and a large, golden teapot comes alive and shoots a rainbow from its spout. A cartoon version of the girl then slides along the rainbow and, interpreting the lyrics of the song, catches a falling star and rides over the moon.

By the second verse, pink elephants float over the girl’s bed and an animated fairy version of Madonna emerges from the picture and winks. She takes the girl through another picture, displaying mythological and fairytale beings such as dragons, princes and unicorns as well as a castle where Madonna dances with the moon. An underwater scene with mermaids and fish follows, then a parade of all the girl’s toys around her room. As the song wraps, the fairy taps on the girl and causes her to yawn. She falls asleep again and her toys go back to being as they were. The violins and the instruments gradually fade inside the radio and the song ends.


Tracks
1 Dear Jessie. 4:20
2 Till Death Do Us Part. 5:09
3 Holiday (12” Version). 6:04

Madonna

1989

16

075992142120

United States

CD

45 rpm

Single

W2668CD

3.5

Johnny Yuma Studios in Burbank, California

3

Single

320 kbit/s

1

2018-06-28 16:15:16

Slimline Case

Studio Single

26

~$18.98

2025-10-23

2018-06-28 16:15:16