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.