124 SCORE: 7.3 2015 PLACEMENT: UP 8 - 132 of 210 (6.689) HIGHEST SCORE: 10 x 6 (@fatyoshi @BreatheBox @scottdisick94 @joeee @phoenix123 @TheChoirgirlHotel) LOWEST SCORE: 3 x 3 (@Babyface @VeryPSB @KingBruno) MY SCORE: 5/10 Another song that has maybe been flying under the radar for a while, but most likely an inevitable casualty of our surge into Top 100. Some of y'all are going to drag me for my score but you know that this kind of saccharine nonsense was never going to fly with me no matter how lovely Madonna sounds on it. Part LSD trip and part children's lullaby, this was somehow a single from Like A Prayer despite there still being options that weren't, you know, this. However, what do I know? It stayed in the Top 5 for three weeks in the UK so it clearly struck a chord. I will cop to the origin story being adorable though. Patrick Leonard was late to the studio one day because he had to pick up his young daughter, the titular Jessie. He decided to bring her to the studio since he was already running late for Madonna, who was furious at his tardiness (SIS the hypocrisy!) and most likely came close to breathing fire on the diminutive woman that Patrick had the nerve to arrive with, before she realised it was a child. Madonna, in a rare moment of softness, was completely and utterly beguiled by her, to the point that Patrick approached her with a song he had been writing for his daughter, and Madonna agreed to sing it and put it on her upcoming album, the now-iconic Like A Prayer. Although I don't think that was their first meeting, at least going by this quote in Q Magazine in 2015 from Patrick Leonard himself. Considering the dates and the fact that he directed the Who's That Girl Tour, this must have happened before the recording of "Dear Jessie" a year later. Do you have a favorite Madonna memory? Yes. When we were on tour. We were in London and it was her birthday. There was a private party in a club, and all these people wanted to dance with her and hang out with her, and Jessie, my daughter, was with us on tour at that time. She was right around 2 years old. You can find things in the press that are still out there — Madonna sat her up on the bar and put half a glass of champagne in her, or a couple of sips or whatever it was, and danced with her pretty much all night. Jessie stood in the middle of the dance floor and spun in her dress, and the next day you saw all these things in all these tabloids with all these faces of celebrities who wanted to dance with her, and Jessie was their foil all night. That was really fun to just see her embrace my daughter and have fun like that. It was really, really special. There are a lot of memories. She’s a good girl. Madonna is a good girl. Patrick Leonard remains such a class act. The song only received an animated video, in which Madonna appears as a fairy weirdly styled as her Who's That Girl self despite her being deep into a new era look by that point. I maybe thought it was because the Blond Ambition Tour had started or because she was filming Dick Tracy, but both of those things happened well before and well after, so if anyone knows why, feel free to tell us why! It's suitably trippy for a song about pink elephants and lemonade. And while Madonna herself has never performed it live, Patrick Leonard performed an instrumental of it in 2017 at a concert of his own, where he broke down various Madonna co-writes and spoke a little about them. Cute!