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Released in early summer of 1986, Madonna’s third album, True Blue, reflects major changes in her star status since its predecessor, Like A Virgin. She was now a world-class celebrity, married to actor Sean Penn and living in a Beverly Hills mansion. Indeed, True Blue was dedicated ‘to my husband, the coolest guy in the universe’.

The cover portrait, by Herb Ritts, shows Madonna in profile, and has a timeless beauty. The ‘boy-toy’ of old is gone, or at least toned down. She is shown in sepia tones, with tinted lips and eyelids, against a sea-blue background. The song titles are handwritten on the back, and the inner sleeve includes lyrics. The simple, bold design emphasises substance over style.


The first song, ‘Papa Don’t Preach’, begins with a string arrangement, leading into Madonna’s strongest, most soulful vocal to date. It was written by Dave Elliot, and deals with nascent sexuality as ‘Like A Virgin’ did, but with less flippancy. This song tells a story, of a teenage girl who becomes pregnant and decides to keep the baby, supported by her boyfriend. But it is not to her lover that she is pleading, but her disapproving father. The video is directed by Mary Lambert, who also made ‘Borderline’, ‘Like a Virgin’ and ‘Material Girl’. 27 year-old Madonna somehow manages to look no more than fifteen, and her acting, like her singing, is raw and emotionally honest.


‘Open Your Heart’ was adapted by Madonna and Pat Leonard, who also co-produced the album (with Madonna and her longtime collaborator, Steve Bray.) Their partnership is one of the most significant in Madonna’s career and allowed her to make the difficult transition from pop sensation to credible singer-songwriter. Madonna’s pursuit of a stubborn lover (perhaps inspired by Penn), throughout the track is full of energy and joy, another classic pop single. In the video, directed by photographer Jean-Baptiste Mondino, Madonna plays an exotic dancer at a peep-show, who eventually runs away with a young boy. The visuals reference the paintings of Tamara De Lempicka.

A snippet of dialogue from James Cagney in the 1949 gangster movie, White Heat, opens the third track which bears the same name. Madonna’s fascination with Hollywood mythology made her marriage to Sean Penn, a latter-day ‘bad boy’, almost inevitable. Sampling dialogue was a relatively new practice then, and Madonna continued the gangster schtick when performing ‘White Heat‘ on tour. It’s another brisk dance workout, and a warning of storms ahead: ‘I’m not gonna live out your fantasy/Love’s not that easy…’


After playing opposite her husband in the ill-fated Shanghai Surprise, Madonna contributed musically to the critically acclaimed At Close Range, starring Penn and Christopher Walken. ‘Live To Tell’ is a sombre ballad, unlike anything she had done before and a brave choice for the first single. The lyrics are enigmatic – ‘I know where beauty lives/I’ve seen her once, I know the warmth she gives/The light that you could never see/It shines inside, you can’t take that from me.’ Madonna could be referring to her struggle to survive fame, or something buried deeper in her past. Whatever the inspiration, its appeal is universal.

‘If I ran away, I’d never have the strength/To go very far,’ she confides, ‘how will they hear the beating of my heart?’ There is a sadness and vulnerability here which is a world away from the swagger of ‘Material Girl’. It has a frailty that Madonna reveals only rarely, in her music, but it is enchanting. In the video, she sings against a dark backdrop, interspersed with clips from the film. And ‘Live To Tell’ is used effectively in At Close Range, part of the action rather than an afterthought. It shows a maturing artist who is capable of relinquishing the spotlight and letting her talent speak for itself.

The mood changes abruptly with ‘Where’s The Party‘, a light-hearted dance track. Some production weaknesses show up here, with the tinny, over-synthesised sound that is so typical of mid-eighties pop threatening to take the heart out of the song. But it’s still fun to listen to, and the lyrics suggest a stressed-out working girl yearning for more carefree days.


The title track, ‘True Blue’, follows, perhaps the most obvious ‘valentine’ to Sean Penn. Musically, it is modelled on the girl-group sound of the early sixties, and largely succeeds despite the ever-present synthesisers. The video was directed by Penn’s friend James Foley, who also made At Close Range and would helm Madonna’s next film, Who’s That Girl. Her heartfelt vocals supplant any innate goofiness, which is (arguably) part of its charm. ‘I’ve had other guys/I’ve looked into their eyes,’ Madonna admits. ‘But I never knew love before/Till you walked through my door…’


‘La Isla Bonita’ was the final single from the album, an instant holiday hit and revived on her tours to this day. Originally written for Michael Jackson, it was reworked by Madonna and Pat Leonard. It marks the beginning of her love affair with all things Latino, musically speaking (Madonna is herself half-Italian.)

‘Last night I dreamt of San Pedro,’ she sings. ‘It all seems like yesterday, not far away.’ At the heart of this song is another story, of her yearning for the ‘beautiful island’ of San Pedro. Bruce Gaitsch contributes a lovely Spanish guitar melody, and Madonna’s vocal is sweet and wistful. In the video (directed by Mary Lambert), she takes on two personas – the young girl in prayer, lighting a candle, and the street senorita dancing in a sumptuous red dress.

The next track, ‘Jimmy Jimmy‘, shows Madonna taking on a teenage persona once again. She is the smalltown girl trailing after a rebel lover; a James Dean type, or perhaps Sean again. Its retro-kitsch style is reminiscent of ‘True Blue’, but less effective. The album closes with ‘Love Makes The World Go Round‘, originally performed at Live Aid in 1985. On that day, it was a crowd-pleaser, but a second hearing does the treacly lyrics and peppy production few favours.


With True Blue, Madonna created five of her most memorable singles, and though as a whole the album is uneven, it represents a high point in her ascent from aspirant to genuine icon, with hits like ‘Papa Don’t Preach’ and ‘La Isla Bonita’ putting her on a par, commercially and even artistically, with the most successful of her peers. Unused tracks include ‘Each Time You Break My Heart’ – a hit for Levi’s model Nick Kamen – and ‘Spotlight’, co-written with Curtis Hudson (who gave Madonna her first hit with ‘Holiday’), resurfaced on her 1988 remix album, You Can Dance.

In 1987, she released four new songs on the soundtrack for Who’s That Girl – which proved more popular than the movie – and embarked on her first world tour. By March 1989, when Like a Prayer was released, the Penns’ rocky marriage was over.

The youthful optimism of True Blue proved hard to recapture, but in recent years, Madonna has reworked those early pop gems. For her Drowned World Tour in 2001, she showed off her guitar skills with an acoustic ‘La Isla Bonita’. She wore a ‘Kabbalists Do It Better’ t-shirt with a kilt while singing ‘Papa Don’t Preach’ on her 2004 Reinvention Tour, referencing her ‘Italians Do It Better’ tee from the iconic video.

Her performance of ‘Live to Tell’ on a Swarovski diamond cross during 2006’s Confessions Tour drew censure from religious groups, while her son Rocco took the boy’s role in ‘Open Your Heart’ for the MDNA Tour in 2012. Perhaps the most poignant revival, though, was ‘True Blue’ played on a ukulele during her Rebel Heart Tour in 2015 – with ex-husband Sean Penn, to whom Madonna remains close, in the audience.