On December 30 1989, Dear Jessie peaked at number-five on the UK singles chart. The track was released as the fourth single from Like A Prayer in Europe (with the exception of France which instead opted to service the North American/Japanese fourth single, Oh Father) and as the fifth single in Australia.
Dear Jessie was written and produced by Madonna and Patrick Leonard and was inspired by Leonard’s young daughter, Jessie, with whom Madonna had developed a special connection.
The psychedelia-infused reflection on childhood fantasy and innocence was particularly poignant within the context of the Like A Prayer album’s sequencing, with its segue into Oh Father offering a stark musical and emotional contrast that is perhaps one of the most effective in Madonna’s body of work.
On December 24 1995, Oh Father was released as the second UK single from Madonna’s ballads retrospective, Something To Remember.
Warner had initially declined the option to release Oh Father in most European markets when it became the fourth North American single from Like A Prayer in late 1989, instead opting for a more by-the-numbers portrait of childhood innocence with the release of Dear Jessie. Why it was determined to be a better idea in 1995, following its poor showing on the U.S. charts, is anyone’s guess. One possibility is that Oh Father‘s brilliant preexisting music video provided an easy, cost-free means of promoting the song while Madonna remained unavailable due to her recording commitments for the Evita soundtrack.
While I would personally rank Oh Father among Madonna’s very best musical and lyrical efforts, and its music video an underrated classic – it never had the makings of a commercial hit. And history repeated itself when the song’s dark subject matter once again stunted its ability to gain momentum on radio for its British release. It became only her third UK single at the time to peak outside the top-ten when it stalled at #16 in its first charting week. It fared better in Finland and Italy, however, reaching #6 in both countries.
On December 19 1987, Madonna’s haunting ballad The Look Of Love peaked at number nine on the UK Singles Chart. The third and final Madonna single from the Who’s That Girl soundtrack, it was released only in select European countries and in Japan.
The Look Of Love was written, produced and recorded by Madonna and Patrick Leonard during the second of a three-day studio session, with the title track of the soundtrack being written and recorded on the first day. Additional musicians were brought in for overdubs and mixing was completed for both tracks by the end of the third day.
Despite being a set-list staple on the Who’s That Girl tour – the song’s limited release, moderate chart success, along with the fact that it has not been included in any of Madonna’s subsequent retrospective collections has led to it being largely forgotten, although fans frequently cite it as an underrated gem.
In a 1991 interview with ICON magazine, background vocalist Niki Haris expressed fond memories of performing the track with Madonna during the 1987 tour:
“My favorite song ever to perform with Madonna was a song called The Look Of Love from the Who’s That Girl Tour [Niki sings: Nowhere to run, nowhere to hide…]. That is one of the greatest songs and Madonna sings it really great. That’s my favorite song of all time as far as singing with her.”
The single reached number six in Ireland, number eight in the Netherlands and number ten in Belgium, while it peaked outside the top-ten in Germany, Switzerland, France and Japan.
On November 24 1990, Madonna’s first greatest hits collection, The Immaculate Collection, hit #1 on the UK album chart, and was the biggest selling album in the UK by a female (certified 12x platinum for sales of 3.7-million copies) until Adele’s 21 took over the top spot (certified 16x platinum for sales of 5-million copies).