Albums: Who’s That Girl (1987), Celebration (2009)
Songwriters/producers: Madonna/Patrick Leonard

To me, the entire Who’s That Girl era (tour excluded) is one of the few phases in Madonna’s career where she was more regressive than forward-thinking. Though popular enough to warrant inclusion on Celebration (but not on the Immaculate Collection, thankfully), it’s hardly on the level of True Blue’s five deeply consistent singles. The backing sounds closer to Stephen Bray’s co-writes (via La Isla Bonita’s Latin feel) than Patrick Leonard’s own generally moodier compositions - and it succeeds as a movie theme, but not so much at attempting Bray’s more rhythmic style. As effectively quirky as the Spanish phrases, flourishes and bouncy bassline are, whimsical simply can’t compete with the more compelling intensity Madonna delivered for much of the decade. Nevertheless, it didn’t stop Who’s That Girl from becoming Madonna’s sixth US Billboard chart-topper.

Ironically, nor could the overwhelming success of the eponymous song or tour ensure the same for the film. Who’s That Girl is a strange beast - coming after Madonna’s first “serious” acting role alongside Sean Penn in the critical and commercial flop Shanghai Surprise, it was an odd choice considering she needed more than ever to prove herself. It shares many similarities with Desperately Seeking Susan - from Madonna’s impulsive characters to the ludicrously complex plot - but with an awkward screenplay and dialogue that make it instant bait for a critical panning. However, the film’s not short on gags (some unintentional) or personality - playing ex-convict Nikki Finn, Madonna manages to both not derail the film into a vehicle for her real-life persona and make the absurd, grating Noo Yawk squawk of a character into something genuinely endearing by the end. The ’80s excess of Who’s That Girl, though convoluted and at times utterly ridiculous, can be an enjoyable watch provided you check your logic at the door.

HOWEVER. With no real sense of credibility, Who’s That Girl did little to further Madonna’s reputation as an actress. Fun enough to satisfy its young target audience, but otherwise, the film wasn’t a success on a critical, financial or career level.

Yet again, the music video has two different Madonnas - Nikki Finn shown in footage from the film, and a more girlish continuation of the oversized tuxedo-wearing Madonna from Open Your Heart. She really just lipsyncs and dances along with some randoms - fun at best, but there’s not much personality on show (and Nikki Finn just looks strange out of context).