“Dear Jessie” is a whimsical and dreamy song by Madonna, released in December 1989 as the fifth single from her fourth studio album, Like a Prayer (1989). Written by Madonna and her frequent collaborator Patrick Leonard, the song is a notable departure from her typical pop sound, embracing a fairy tale-like atmosphere with orchestral arrangements. “Dear Jessie” was inspired by Leonard’s young daughter, Jessie, and features childlike imagery and a playful tone. Although it was not released as a single in the U.S., it achieved commercial success in Europe, especially in the UK, where it reached No. 5 on the UK Singles Chart.
“Dear Jessie” originated during Madonna’s collaboration with Patrick Leonard for the Like a Prayer album. The song was inspired by Leonard’s daughter, Jessie, with whom Madonna was reportedly close. The lyrics are filled with vivid, fantastical imagery, reflecting the innocence and wonder of childhood. Madonna’s decision to include such a whimsical track on an album known for its introspective and mature themes highlights her versatility as an artist.
The lyrics of “Dear Jessie” describe a magical world of pink elephants, lemonade lakes, and dancing moons, evoking the wonder and imagination of a child’s dreams. Lines like “Pink elephants and lemonade, dear Jessie, hear the laughter running through the love parade” create a sense of whimsy and nostalgia. While the song can be interpreted as a simple lullaby or fantasy, it also reflects broader themes of joy, innocence, and escapism, offering a lighthearted counterpoint to the more serious tracks on Like a Prayer.
“Dear Jessie” is a baroque pop song with orchestral arrangements and a light, dreamy quality. The production, helmed by Patrick Leonard, incorporates strings, woodwinds, and synthesizers to create a whimsical and ethereal soundscape. The song’s waltz-like rhythm and layered harmonies further enhance its fairy tale-like charm. Madonna’s vocal delivery is soft and tender, blending seamlessly with the lush instrumentation. Her voice conveys warmth and playfulness, perfectly capturing the song’s childlike essence.
“Dear Jessie” was released as a single in Europe, Australia, and Japan, but not in the United States. In the UK, it peaked at No. 5, becoming Madonna’s 17th consecutive top 10 single there. The song also charted in the top 10 in several other European countries, including Ireland and Belgium, and achieved moderate success in Australia. Although not as commercially dominant as some of Madonna’s other hits, “Dear Jessie” demonstrated her ability to experiment with different styles and themes.
The music video for “Dear Jessie** was an animated fantasy directed by Derek Hayes. It features Madonna as an animated fairy interacting with a young girl named Jessie in a colorful, magical world. The video includes imagery of pink elephants, castles, and flying unicorns, bringing the song’s lyrics to life. The animation style is reminiscent of classic children’s cartoons, reinforcing the song’s whimsical and nostalgic tone. The video received airplay in regions where the song was released as a single, further enhancing its appeal.