Albums: True Blue (1986), The Immaculate Collection (1990), The Confessions Tour (2007), Celebration (2009)
Songwriters: Madonna/Patrick Leonard/Bruce Gaitsch
Producers: Madonna/Patrick Leonard

Though at this stage of her career, Madonna had appropriated/reinterpreted - not copied, of course - the likes of Marilyn Monroe and Audrey Hepburn’s classicist images before, La Isla Bonita was the first of various times she’d take on an entire culture. La Isla Bonita is the sound of a time and a place as much as it is one of the first Latin-flavoured pop songs to truly enter the Western consciousness. Songwriters Patrick Leonard and Bruce Gaitsch originally offered the song to Michael Jackson, though it was rejected, and probably for a good reason. Madonna’s vocal performance (especially the dreamy backing vocals) necessarily removes the focus from herself to suit the song’s mood in a way that’s hard to imagine MJ pulling off quite as convincingly, incredible talent aside. What makes the song so successful is how effortlessly it creates a Latin feel; despite being as driven by synths and drum machines as much as any ’80s pop song, the acoustic guitar and Cuban drums still make the most lasting impression. It’s both moody and exotic; light but never disposable like Holiday, and incredibly vital for the fifth(!) single and top-five hit from True Blue.

(for anyone still unconvinced of Madonna’s vocal abilities, compare the original to this competent yet entirely robotic cover by singer Alizée, whose version inexplicably reached number two on her native French charts)

La Isla Bonita is an odd nomination for one of Madonna’s most enduring live songs - but aside from the rather flat, slowed-down Drowned World Tour version, the recent re-inventions are all excellent. Turning a mildly elegiac memory as a song into a sped-up international party sounds like a terrible idea, but the Confessions Tour version segues into a percussion/dance breakdown to great effect. Her Live Earth performance takes that direction to its logical(?) conclusion with an unlikely collaboration with Gypsy punk band Gogol Bordello, with the Sticky & Sweet Tour version even segueing into the genuine Romani-Gypsy folk song Doli Doli. It says a lot about the skill of the original songwriting, the current arrangements and Madonna’s live performances that it sits so well aside sets full of far more disco/hip-hop/electronic-influenced songs.

The music video is one of Madonna’s most lushly romantic - even if its setting is more streetside than island. It disregards the song’s love story for a greater focus on image that nonetheless fits the song perfectly. As with Papa Don’t Preach and Open Your Heart, Madonna again embodies two different images - a restrained religious girl and an incredibly passionate dancer, she of the jaw-droppingly stunning red flamenco dress. The former stays in her room and sheds a tear watching the outside celebrations, praying at what seems to be a shrine to (dead?) relatives, whilst the latter leaves an apartment with mostly candles as residents to dance with the locals on the street. On one level, it could be Madonna’s commentary on the way religious dedication - separate from spirituality - restricts people’s lives, but it doesn’t condemn, instead treating both characters with equal respect. But as with many of her videos, it gets by on sheer beauty regardless of how conclusively it’s understood.