Madonna’s third studio album, True Blue is one of the best-selling albums of all time. Released this month in 1986, it was an immediate global smash with all five singles from the album – “Live to Te Tell”, “Papa Don’t Preach”, “True Blue”, “Open Your Heart” and “La Isla Bonita” – reaching number one in either the U.S. or U.K., with “Papa Don’t Preach” topping both! 

Dedicated to then-husband Sean Penn, the True Blue track listing delivered some torch songs, alongside some self-penned affirmations to her growing ambition. The album’s five singles all arrived with slick, high-budget music videos that earned her a Video Vanguard Award at the 1986 MTV Music Video Awards, making her the first female artist to ever receive the award. 

With over 25 million copies sold worldwide, True Blue cemented Madonna's status as a superstar. In honour of the album’s 35th anniversary, let’s remember those award-winning music videos below. 

Madonna | “Live To Tell”

Speaking of Sean Penn… Lead single “Live To Tell” appeared in the actor’s 1986 neo-noir, At Close Range, with the music video featuring scenes from the film intercut with Madonna’s performance. It also gave us our first glimpse of the singer’s classic Marylin Monroe inspired Hollywood blonde makeover featured on the album’s iconic Herb Ritts cover photo.

Madonna | “Papa Don't Preach”

“Papa Don’t Preach” tells a story of teen pregnancy and the choices that come with it. The music video doubles as a 5-minute short film as Madonna struggles to tell her father, played by Danny Aiello, that she’s pregnant. The storyline is juxtaposed with shots of Madonna performing in a small, dark studio in a very Greece-inspired outfit… 

In true Madonna form, the song attracted its fair share of controversy when it was first released, for the fact it was seen to advocate teen pregnancy. But that didn’t stop it from going number one in multiple countries around the world. 

Madonna | “True Blue”

Any controversy was wiped clean with this wholesome, 50s inspired ode to true love. 

Madonna | “Open Your Heart”

Until she dropped this bombshell! In this cinematic peepshow, Madonna plays an exotic dancer who befriends a young boy with whom she escapes and she dances off into the sunset. 

Again, she received some criticism for depicting a child waiting outside of a strip club, but in a retrospective of her controversial moments, this one barely rates. 

Madonna | “La Isla Bonita” 

Spanish for ‘the beautiful island’, “La Isla Bonita” brings a complete scene change. The Latin lullaby sees Madonna Flamenco dancing her way through the street in a strikingly embellished red Spanish dress. The video first appeared on MTV in March 1987 and became the most requested video in the channel history by a record-breaking 20 consecutive weeks!

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