Album: Vision Quest (1984)
Songwriter: Madonna
Producer: John “Jellybean” Benitez

In a parallel universe, after Gambler became her sixth UK top ten single in 11 months, one Madonna Louise Veronica Ciccone took her success for granted. Growing complacent, she released one similar crowd-pleasing single after another, eventually oversaturating the market and fading into the background of stock-standard ’80s pop she never truly originated from.

(this is Gambler’s appearance in Vision Quest, leading into Crazy for You; here’s the music video, once again compiled of clips from the film)

The song’s role as part of Vision Quest is essentially filler to soundtrack the nightclub scene until Crazy for You draws the audience in. In that sense, it fulfils its purpose - but was it ever originally intended to be a single? It’s not really bad… but ironically, for a song Madonna wrote alone, she invested little of her own personality into it. Gambler sounds, more than anything, like a Pat Benatar outtake - even with passionate vocals, the songwriting wasn’t strong enough to justify its release as a single for any reason other than high levels of demand for more Madonna product. Though in the long term it neither really did nor prevented any harm, Gambler - recorded under Geffen - was never released as a single in the US, likely due to fears by Madonna’s usual record label Sire that it’d detract from all her other charting singles at the time. But thankfully, their precautions were in vain - only five months later, Madonna would drop the game-changing Live to Tell’s quiet storm on the world, forcefully reasserting her relevance. Back then, Gambler was generic, and is now even more so; though fans may complain, it’s easy to see why it was never rereleased on any of Madonna’s compilations or albums.