Dear Jessie was the fifth single off of the Like a Prayer album, but it was only released in the UK, Australia, Japan and select European countries. The US did not get an official release, instead getting Keep It Together. By far the most sugary sweet of any Madonna song, Dear Jessie was written by Madonna and frequent callaborator Patrick Leonard, inspired by Leonard's daughter, Jessie. The song is more of a lullaby than a pop song, but the theme of it fit perfectly into the Like a Prayer album, sandwiched between the joyous Cherish and the darker Oh Father, which used the string section at the end of Dear Jessie to seque into its own. The song reached #5 in the UK in the winter of 1990. The video for the song features Madonna only in cartoon form, as a short-haired, Tinkerbell-esque character floating through the room and imagination of a little girl. It's really cute, y'all! Enjoy Dear Jessie and have a great Madonna Friday!