Dear Jessie

"Dear Jessie" was the fifth single by American singer-songwriter Madonna from her 4th studio album Like a Prayer and was released on December 10, 1989 by Sire Records. It was released only in the UK, some European countries and Australia.

Song information

The song was inspired by co-writer Patrick Leonard's daughter, Jessie.

The single sold strongly in the UK during the Christmas period peaking at #5 with sales of 250,769. The song did not receive a worldwide release. It was not released in France, North America, Latin America and Asia. For this reason, it was her poorest selling single since "Gambler" in 1985.

The chorus of the song was used for the successful 1999 single "Dear Jessie" by a German Eurodance-project called Rollergirl.

Dear Jessie was the last Madonna song released in the 1980s, the decade that gave her fame, fortune and a launching pad for a career which lasts to the present.

Music video

The music video was produced by Animation City, an animation company in London, England and directed by Derek Hayes. The video does not feature Madonna, except as an animated fairy. Although never commercially released, it was included on the 1990 promotional-only video compilation She's Breathless.

  • Director: Derek Hayes
  • Producer: Maddy Sparrow
  • Animators: Jimmy Farrington, Andy Goff, Derek Hayes, Alison Snowden
  • Production Company: Animation City

Track listing

7" Single/7" Picture disc

  • Dear Jessie
  • Till Death Do Us Part

12" Single/12" Posterbag/CD Single/CD Picture Disc

  • Dear Jessie
  • Till Death Do Us Part
  • Holiday (12" Version)

Official versions

Official versions

  • Album Version (4:20)


  • Flange's Tribal Parade Mix (7:57)


Chart (1989/1990) Peak
Australia 41
Austria 21
Eurochart Hot 100 9
Germany 19
Netherlands 25
Ireland 3
South Africa, Republic of 9
Spain 17
Switzerland 16
United Kingdom 5

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