Madonna – Dear Jessie (1989) Madonna 1989 Dear Jessie Did you know that... In 2019, Madonna had had a hit in the UK Top 40 every year since 1984 (except for 1988, 2004 and 2007). She is probably the most successful female artist ever, having sold more than 200 million albums. How does this song make you feel? Report abuse SHARE THIS WITH YOUR FRIENDS