The album to start with
Like a Prayer (1989)
Madonna’s 1980s hits such as Holiday, Into the Groove and Like a Virgin are brilliantly captured on The Immaculate Collection (1990). If you want a deeper exploration of her musical psyche and kinetic songwriting though, I’d advise listening to the post-True Blue albums. In the late 80s, having conquered the charts with 19 hit singles, she was ready to challenge herself with more personal lyrics and a richly collaborative approach with her producers and musicians. Dubbed her “divorce album”, 1989’s Like a Prayer was recorded at the worst point in Madonna’s marriage to Sean Penn, as the giddy pace and crashing glass of Till Death Do Us Part testifies.
As well as capturing the emotional chaos of her marriage, Madonna delved into her Catholic girlhood and family dynamics with some Freudian pop songwriting. Producer Pat Leonard was the yang to Madonna’s yin, his deeply melodic music providing the ballast for her vivid lyrics. The standout song here is easily the iconic title track, with its fiery gospel choir, Guy Pratt’s runaway bass line and the lyrical celebration of the sacred and profane. Also lovely is the tender piano ballad Promise to Try (in memory of her mother), and Express Yourself – a funky, feminist call to arms that she wrote with Stephen Bray, stepping out, as he put it “like Daenerys in Game of Thrones, emerging from the fire”.
The three to check out next
Ray of Light (1998)
Recorded in her late 30s, after the birth of her daughter Lourdes, 1998’s Ray of Light marks out Madonna’s maturity as an artist. Study of Kabbalah and yogic philosophy had taken her down an experimental path, and William Orbit’s trippy, electronic production created the space for questing lyrics about the death of the ego and personal transformation. Singing a set of robust, theatrical songs for the Evita movie soundtrack two years earlier had made Madonna’s voice stronger and more expressive – especially for the techno-driven title track, in which Orbit made her sing a semitone above her comfort zone.
This record is a triumph, more of a concept album than a collection of songs. It’s not just Orbit’s icy production that makes it so rewarding, but Pat Leonard’s dramatic arrangements for tracks like Frozen and Nothing Really Matters (the latter featuring glorious backing vocals by Donna De Lory and Niki Haris). There is a sense of personal revelation in the chilling final track Mer Girl, where Madonna creates a poetic, nightmarish vision of her dead mother buried beneath the earth.
The album won her four Grammys, and conclusively proved her worth as a musician and executive producer, willing to take artistic risks. On the track Nothing Really Matters, for instance, Orbit wanted to get rid of co-producer Marius De Vries’ strange, strangled intro. “Sounds like a broken DAT,” he protested. Madonna, who had the casting vote, kept the noise in, adding another layer to the album’s futuristic, otherworldly sound.
Driven by producer Mirwais Ahmadzaï’s fractured disco and acid bass, the opening track is classic party Madonna. “Music makes the people come together / Music makes the bourgeoisie and the rebel.” What a fantastic line – and, sung in that choppy, insouciant way, one of most memorable in 2000s pop. On this album, Madonna explores what love and music mean to her, moving easily from the sinuous country grooves of Don’t Tell Me to the space age ambience of What It Feels Like For a Girl (complete with Charlotte Gainsbourg’s soft spoken-word intro). What’s most striking now is the track Paradise (Not for Me). Somewhat overlooked at the time of the album’s release, with its pitch-shifting chanson, trip-hop bedroom pop and melting strings, it’s very of this pop moment.
Madame X (2019)
Madonna went a little off the boil after 2005’s Confessions on a Dance Floor with a few albums (Hard Candy, MDNA, Rebel Heart) where she seemed less engaged, less excited. With last year’s Madame X, she rediscovered her mojo. Reflecting on her new life in Lisbon, this album is about exile and liberation, incorporating everything from reggaeton, mournful Portuguese fado and devotional Moroccan Ganawa to trap-inspired hip-hop. Dark Ballet (produced by Mirwais) has a rococo brilliance, while I Don’t Search I Find is an almost mystical return to the dancefloor. And Batuka, performed with the mighty Orquestra Batukadeiras, has a dark, percussive female power. When you think about where Madonna began, with the heady New York beat box sound of 1982’s Everybody, hers has been an amazing journey.
One for the heads
Sorry (Pet Shop Boys Maxi Mix, 2006)
Sorry is the best song on Madonna’s disco-inspired Confessions on a Dance Floor. The radio version is throwaway, flippant and arch, but this eight-minute Pet Shop Boys remix brings out a whole new layer of meaning, emphasising the drama behind Madonna’s words. Just after an enticing build-up comes Madonna’s quietly menacing vocal, and the PSB’s plaintively apologetic: “I’m sorry … so sorry.” Thunderous – and my favourite remix ever.
The primer playlist
Madonna’s Private Diaries, by Madonna, Vanity Fair
One of the few extended pieces of writing by Madonna. It’s a fascinating journal, written while she was filming Evita in Argentina, pregnant with Lourdes. “I wonder if I could ever have been the kind of sweet, submissive, feminine girl that the entire world idealises,” she muses.
Power is an Aphrodisiac, by Danny Eccleston, Q magazine
Eccleston’s down-to-earth humour brought out a different, less guarded Madonna in this free-ranging interview.
Madonna at Sixty, by Vanessa Grigoriadis, New York Times
A thoughtful, analytical study, in which Madonna discusses Trump, Time’s Up and being a feminist heroine. She also quotes the American poet Mary Oliver: “When it’s over, I want to say: all my life I was a bride / married to amazement. / I was the bridegroom, taking the world into my arms.”
• Lucy O’Brien is the author of Madonna: Like an Icon (Corgi), available now.
This article contains affiliate links, which means we may earn a small commission if a reader clicks through and makes a purchase. All our journalism is independent and is in no way influenced by any advertiser or commercial initiative. By clicking on an affiliate link, you accept that third-party cookies will be set. More information.