Album: Like a Prayer (1989)
Songwriters/producers: Madonna/Patrick Leonard

The question I believe everyone asks themselves upon hearing Dear Jessie for the first time is “…why?” If the greatest sex symbol (and so much more) of the ’80s wanted to prove once and for all her mettle as a serious adult artist, why did she write and release a kids’ lullaby? Why, on Like a Prayer, was it sandwiched between the album’s purest pop song and its most serious, heart-wrenching ballad? And why was it released as a single at all, let alone Madonna’s final single of the 1980s?

Dear Jessie was originally inspired by Jessie, Patrick Leonard’s daughter - though the idea and most of the music was likely his, how its collaboration and recording with Madonna came about remains a mystery. Though the Beatles’ Sgt. Pepper’s Lonely Hearts Club Band is always mentioned as a reference point, to me the overall feel is closer to Disney’s iconic Fantasia - perhaps referenced by Madonna’s Minnie Mouse ears on the single cover - albeit with the colours flipped around, the general sense of darkness removed. In the sense that Dear Jessie was intended as a lullaby to a young girl, it works fine, but the “pink elephants and lemonade” imagery that makes up the song is just gratingly cutesy to adult ears. The same goes for the music, which is so bright and major-key it’s saccharine - but at least the composition and fluttering string arrangements are complex enough to make the song an interesting, maybe even a rewarding listen.

So standalone, the song achieves what it aims for - but why its inclusion on Like a Prayer? Compared to Promise to Try, Madonna’s powerful, bittersweet dedication to her motherless childhood self, Dear Jessie comes off as both musically weaker and insincere escapism coming from a woman who’s lived the fact that childhood is not always innocence and happily-ever-after. And though the segue between the two songs helps, putting Dear Jessie right before Oh Father practically invites listeners to think less of the prior track. But in asking why, one has to consider that Dear Jessie was written for a child - and that Madonna would certainly never have wished her own hardship on anyone else’s, let alone her own. Though she had good intentions, one wishes the song wasn’t so jarring as to detract from the flow of the overall album. To hear her write truly mature, uncontrived music for a child, we’d have to wait nearly a decade for the birth of her daughter Lourdes, the inspiration behind the genuinely affecting Little Star… and another few years for the English Roses, her series of children’s books with morals! (if you’re into that kind of thing)

With all this considered, why was Dear Jessie released as a single - infuriatingly, instead of the far more deserving Oh Father in the UK? Well, it came out on the 10th of December, and perhaps as a result of the end-of-year spirit, it may have tapped into the Christmas market more than the Madonna market, peaking at #5 in the British charts. And though it’s now barely remembered, it was once fitting as an adopted Christmas song, even if it’s no Winter Wonderland.

The slightly low-budget cartoon music video is, um… appropriate. Hardly MTV fare, and Madonna herself only appears as an animated Tinkerbell knockoff, but the technicolour images admittedly suit the music perfectly - even if for most, they probably turn the whole affair into death by sugar overdose. No wonder it wasn’t included on the Celebration DVD - as much as the fans are completionists, I’m sure nobody really misses it.

(if you’re not convinced and want to feel slightly better about this whole affair, just check out this offensively atrocious Eurodance “cover” of Dear Jessie by Rollergirl, recorded ten years later but already a thousand times more dated)