1989 · Behind the Songs
A lullaby for a producer’s daughter — and a single America never got.
“Dear Jessie” was the fifth single from Like a Prayer (1989), released on December 4, 1989, on Sire Records. It was written and produced by Madonna and Patrick Leonard, and inspired by Leonard’s daughter Jessie. The story goes back to the Johnny Yuma studio sessions in Burbank: while recording the album’s title track, Leonard slipped out to pick Jessie up from school and came back late; Madonna was angry at first, then struck up a rapport with the girl — and Leonard brought her a song he had written for his daughter. It was finished within three days. Built more like a children’s lullaby than a pop song, it runs 4:20 with strings, synthesizer and strummed acoustic guitar, a tempo change and trumpets in the breakdown, and lyrics picturing a psychedelic fantasy world; critics heard the Beatles in it — the New York Times’ Stephen Holden called it a “stylish swatch of late Beatles-style psychedelia.”
It was released only in the UK, parts of Europe, Australia and Japan — never as a US single — with “Till Death Do Us Part” on the B-side. In the UK it debuted at No. 9 on the chart of December 16, 1989, and peaked at No. 5 two weeks later, earning a BPI Silver award; it reached No. 3 in Ireland, No. 9 on the Eurochart Hot 100, No. 19 in Germany across 19 weeks in the Top 100, and No. 51 in Australia, selling 255,000 copies in the UK by August 2008. The video, made by London’s Animation City and directed by Derek Hayes, mixed live action with animation — a little girl, a Tinker Bell-like fairy, pink elephants flying over a bed — and Madonna appears only as the animated fairy; it was included on the 1990 promotional video compilation “She’s Breathless.” The single sleeve used a 1987 Herb Ritts photograph of Madonna in bed wearing Minnie Mouse ears, a nod to the early criticism of her work.