Madonna’s ‘True Blue’: All 9 Songs Ranked

“I used to fantasize that we grew up in the same neighborhood and that he moved away and became a big star,” Madonna told The New York Times in 1966 of her muse for “Jimmy Jimmy,” rebel without a cause James Dean. Although the doo-wop backing vocals on True Blue’s penultimate number provide a touch of the Hollywood icon’s ‘50s era, this musical tribute is still more children’s party than countercultural classic. Madonna’s vocals surely gave the “Minnie Mouse on helium” detractors further ammunition, while the giddy bubblegum synths sound like they’ve overdosed on E numbers. And considering Dean’s tragic fate, the “Why did you go and crash up your new car?” seems a little on the nose.   

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Fans and record label execs alike may have panicked slightly when Madonna unveiled True Blue’s first taster at Live Aid in 1985. (Yes, just like George Michael at the 2012 Olympics closing ceremony, the star used a monumental global event where everyone simply wanted the hits to drop an underwhelming new tune.) Its pleas for peace are undoubtedly well-meaning, of course, but they still succumb to the triteness that plagued “We Are the World.” And while the synthesized horns no doubt aimed for street carnival vibes, they sound like they’ve been lifted from a daytime game show. Thankfully, there was much better to come.   

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Like the proverbial bus, you wait ages for one Madonna song about a silver-screen icon named James and then two come along at once. As its title suggests, “White Heat” is dedicated to James Cagney, the Oscar winner who’d passed away just three months before True Blue’s release. The snatches of dialogue from the same-named 1949 film noir (“And I was gonna split fifty-fifty with a copper/ Maybe they’re waitin’ to pin a medal on him”), along with the actor’s distinctive New York drawl, are undeniably the most interesting thing about a solid but unspectacular blend of juddering funk basslines and rock-lite guitars.   

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“Don’t want to grow old too fast/ Don’t want to let the system get me down/ I’ve got to find a way to make the good times last,” Madonna sings on True Blue’s finest non-single, “Where’s the Party,” a joyous TGIF anthem that sums up her DGAF ethos better than any of the album’s hits. Refusing to cave into the pressures of the pop treadmill and the media whirlwind that had only intensified since getting together with Penn, Madge instead leads a hedonistic rally cry – she practically yells the title – which shows she’s simply going to dance her cares away.   

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Madonna has since reneged on the unashamed romanticism of this marital love letter (“I didn’t know what I was talking about when I wrote it,” she said during a 2015 concert), which perhaps comes with little surprise considering she first filed for divorce just over a year after “True Blue” dropped. Nevertheless, “True Blue” – named after one of Penn’s favorite sayings – perfectly encapsulates the euphoria of an all-consuming romance. The typically composed star sounds positively smitten as she lets down all defenses (“Those tear drops, they won’t fall again/ I’m so excited ’cause you’re my best friend”) on a wonderfully kitsch throwback to the hairbrush-in-the-mirror girl group ditties of the ‘60s. 

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Described by Madonna as a tribute to the “mystery and beauty of Latin American people,” according to Rolling Stone, True Blue’s fifth single was the first time she showcased her love of the culture on record. Sure, its references may be cliched – there’s flamenco guitars, bongos and castanets, not to mention lyrical nods to sambas and siestas and a couple of basic Spanish phrases translated by her Hispanic housekeeper — but Madge still sells her idyllic vision of a mysterious island named San Pedro with warmth and respect. Interestingly, in one of those sliding-doors moments, Patrick Leonard has said that “La Isla Bonita” was first offered to the King of Pop, Michael Jackson, rather than the Queen.

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“Open Your Heart” was initially conceived as a rock n’ roll number for the woman who famously beat Madonna to the best new artist Grammy, Cyndi Lauper. Once again, though, Ms. Ciccone made the song her own, rewriting its lyrics and spinning its sound into a sparkly but muscular progression of her post-disco beginnings. The tale of unrequited love – which introduced longtime backing vocalist De Lory into the fold – deservedly became the album’s third No. 1 and Madonna’s career fifth, a tally that helped her tie with Whitney Houston as the most successful female chart-topper of the decade.  

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Far more memorable than the Penn crime drama it was recorded for (At Close Range), this unexpected torch song should have silenced anyone who doubted ‘80s Madonna’s abilities as a vocalist. While she lacked the powerhouse, octave-spanning tones of her bigger-voiced peers, “Live to Tell” proved she could match – and even surpass – them in conveying genuine emotion. Admittedly, it‘s not difficult to understand why her label bosses may have been reluctant to launch True Blue, an otherwise effervescent pop record, with a deeply foreboding seven-minute ballad that hinted at childhood trauma. But as usual, Madonna’s creative instincts proved spot-on, its dramatic electric piano, fluttering synths and heart-rending melodies kickstarting the album’s trilogy of No. 1s.   

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The story of a young girl defying her father’s orders by keeping her unborn baby, True Blue’s crowning glory was accused of both glamorizing teenage pregnancy and wading into the debate on abortion. As with “Like a Prayer” several years later, the controversy threatened to overshadow the song. But by combining her masterful storytelling with an array of earworm hooks, not to mention a Vivaldian flurry of strings which initially suggested she’d gone all classical, its sound proved to be equally compelling. Resulting in a second Grammy nomination, a fourth career No. 1 and – arguably most significantly – a future brat-rock cover by Kelly Osbourne, this was mid-’80s Madonna at her fearless best.  

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