Album: Like a Prayer (1989)
Songwriters/producers: Madonna/Stephen Bray

As the final single from Like a Prayer, Keep It Together - like Oh Father, unreleased in the UK - never quite managed the zeitgeist-level impact of the album’s first three singles. For where True Blue felt more like a collection of massive, individually brilliant singles, the Madonna on Like a Prayer subdued her larger-than-life persona in service to the more consciously sequenced music. Even Keep It Together, one of the outright catchiest tracks, didn’t sound quite like a radio smash, and perhaps as a result, it took a good two months from its release on the 30th of January, 1990 to peak at #8 on the Billboard charts - only to be swallowed whole as Vogue became something of a cultural phenomenon.

Musically, Keep It Together is pure funk - though very much its own song, it was a less mellow tribute to Sly & the Family Stone, to the extent that Madonna would sing a full verse of their classic Family Affair on the 10-minute version that closed each Blond Ambition performance. Along with Express Yourself, it was her final collaboration with Stephen Bray - so it was natural that they’d mature beyond drum machines for the more complex sounds of pre-disco black popular music. However, the single remix does opt for a more current sound with more piano and synthesised beats, as the album version would’ve sounded rather incongruous on pop radio at the time.

At its core, Like a Prayer is an album about relationships - the spiritual, the romantic, the parental, and on Keep It Together, the familial. Perhaps the most plainly autobiographical lyric Madonna would ever write, it’s practically her life story - from her crowded, oppressed childhood to the even more crowded loneliness of stardom. Through all this, there’s still something fundamentally accepting, sympathetic about her brothers and sisters, who shared her formative experiences of love and loss. But she doesn’t idealise them, either:

But in practice - and more so for the pre-motherhood/Kabbalah Madonna, her actions sometimes spoke louder than words. The above lyrics from Keep It Together effectively sum up her entire relationship with brother Christopher Ciccone, always her closest, most artistically linked sibling, but also the person she cast the greatest shadow upon. From taking dance classes together with Christopher Flynn, to backup dancing in her track dates and Lucky Star video, from dressing and directing her live shows to designing her houses, his life was always defined by his famous sister - to the extent that he found his final independence, rather ironically, in writing his autobiography Life with My Sister Madonna. It’s a depressingly honest read - though very much maligned by certain optimistic fans for his accounts of mistreatment by Madonna’s hand, he admits as much that his resulting life as something of a hanger-on was much better off for her achievements and assistance. And in dedicating The Immaculate Collection to Christopher by his nickname “‘The Pope’, my divine inspiration” - one would hope Madonna acknowledges him in kind.

(Family Affair/Keep It Together live from Japan on the Blond Ambition Tour, complete with bizarre British accent)

The idea of family - literally, and through Madonna’s apparent mothering of her dancers - is central to Truth or Dare (known outside the US as In Bed with Madonna), the 1991 film chronicling the Blond Ambition Tour. To call it a documentary would be wrong - for the mere presence of director Alek Keshishian’s black-and-white cameras created an observer effect, where Madonna would play to the cameras. Hence, there’s little of the honesty on the Like a Prayer album to be found, as the film presents her entire onscreen life as performance art - the dare is the truth. This explains many of the film’s more surreal moments - like her infamous fellating of an Evian bottle, or the simulated sex games with her dancers - but many of the more ordinary scenes are just as put-on. Calling it “the best acting of her whole career”, Christopher Ciccone’s book sheds much light on her less overtly contrived interactions - how brother Marty and childhood friend Moira McPharlin would never have been allowed backstage without cameras, or how he would have waited until after the show to inform her of the Canadian police’s threat to arrest her over obscenity charges. One of the truly sincere moments is Madonna’s tribute to her father, where onstage after the Detroit show, she claims “I worship the ground that he walks on”, and sings Happy Birthday to him with the crowd. On the other hand, the strangest scene comes from visiting her mother’s grave - though the devastatingly honest Promise to Try provides the soundtrack, it’s entirely contrived for the cameras, and perhaps the audience’s sympathy. Christopher looks on with an expression somewhere between bemused and utterly furious; he later wrote “that my sister used my mother’s grave as a movie location, her death as the impetus for her performance, wounds me deeply.”

Overall, Truth or Dare is compelling, entertaining, but highly questionable viewing - perhaps it says a lot that three of her dancers later sued for the film’s supposed invasion of privacy, fraudulent depiction of their private lives and resulting emotional distress. It also created a rift between Madonna and then-boyfriend/Dick Tracy co-star Warren Beatty, who summed up the movie perfectly with the quip that “she doesn’t want to live off-camera”. Personally, I vastly prefer the genuine sincerity of her 2005 Re-Invention Tour documentary I’m Going to Tell You a Secret - though the format is basically the same, the rampant egotism of Truth or Dare’s Madonna at 32 has given way to a 45-year-old at peace with herself and the people around her. Indeed, much of this stems from her family - her beautiful children Lola and Rocco, and her somewhat comically depicted polar-opposite husband Guy Ritchie. Though it’s a shame that relationship didn’t last, I get the feeling she as usual has no regrets - she wouldn’t change it for another chance. Just as the hardship of her childhood molded her into the driven, disciplined personality determined to succeed, her motherhood transformed the self-centered figure into a better, more whole person.

Album: Like a Prayer (1989)
Songwriters/producers: Madonna/Patrick Leonard

The question I believe everyone asks themselves upon hearing Dear Jessie for the first time is “…why?” If the greatest sex symbol (and so much more) of the ’80s wanted to prove once and for all her mettle as a serious adult artist, why did she write and release a kids’ lullaby? Why, on Like a Prayer, was it sandwiched between the album’s purest pop song and its most serious, heart-wrenching ballad? And why was it released as a single at all, let alone Madonna’s final single of the 1980s?

Dear Jessie was originally inspired by Jessie, Patrick Leonard’s daughter - though the idea and most of the music was likely his, how its collaboration and recording with Madonna came about remains a mystery. Though the Beatles’ Sgt. Pepper’s Lonely Hearts Club Band is always mentioned as a reference point, to me the overall feel is closer to Disney’s iconic Fantasia - perhaps referenced by Madonna’s Minnie Mouse ears on the single cover - albeit with the colours flipped around, the general sense of darkness removed. In the sense that Dear Jessie was intended as a lullaby to a young girl, it works fine, but the “pink elephants and lemonade” imagery that makes up the song is just gratingly cutesy to adult ears. The same goes for the music, which is so bright and major-key it’s saccharine - but at least the composition and fluttering string arrangements are complex enough to make the song an interesting, maybe even a rewarding listen.

So standalone, the song achieves what it aims for - but why its inclusion on Like a Prayer? Compared to Promise to Try, Madonna’s powerful, bittersweet dedication to her motherless childhood self, Dear Jessie comes off as both musically weaker and insincere escapism coming from a woman who’s lived the fact that childhood is not always innocence and happily-ever-after. And though the segue between the two songs helps, putting Dear Jessie right before Oh Father practically invites listeners to think less of the prior track. But in asking why, one has to consider that Dear Jessie was written for a child - and that Madonna would certainly never have wished her own hardship on anyone else’s, let alone her own. Though she had good intentions, one wishes the song wasn’t so jarring as to detract from the flow of the overall album. To hear her write truly mature, uncontrived music for a child, we’d have to wait nearly a decade for the birth of her daughter Lourdes, the inspiration behind the genuinely affecting Little Star… and another few years for the English Roses, her series of children’s books with morals! (if you’re into that kind of thing)

With all this considered, why was Dear Jessie released as a single - infuriatingly, instead of the far more deserving Oh Father in the UK? Well, it came out on the 10th of December, and perhaps as a result of the end-of-year spirit, it may have tapped into the Christmas market more than the Madonna market, peaking at #5 in the British charts. And though it’s now barely remembered, it was once fitting as an adopted Christmas song, even if it’s no Winter Wonderland.

The slightly low-budget cartoon music video is, um… appropriate. Hardly MTV fare, and Madonna herself only appears as an animated Tinkerbell knockoff, but the technicolour images admittedly suit the music perfectly - even if for most, they probably turn the whole affair into death by sugar overdose. No wonder it wasn’t included on the Celebration DVD - as much as the fans are completionists, I’m sure nobody really misses it.

(if you’re not convinced and want to feel slightly better about this whole affair, just check out this offensively atrocious Eurodance “cover” of Dear Jessie by Rollergirl, recorded ten years later but already a thousand times more dated)

Albums: Like a Prayer (1989), Something to Remember (1995)
Songwriters/producers: Madonna/Patrick Leonard

The most undeservingly overlooked song of Madonna’s entire ’80s body of work, Oh Father was by far her least commercial single to date. Its original release as a single in late 1989 (excluding the UK, where it was finally released as the second single from Something to Remember in 1995) took guts - predictably peaking at number 20 on the Billboard charts, it ended her run of 16 consecutive top five singles. But it was a necessary sacrifice - for more than sales or populism, the already-world dominating New Madonna wanted respect no matter the cost.

The first shock is how outright lush the song sounds - the piano alone is beautiful enough, but Bill Meyers’ sweeping string arrangement just soars. In a true departure from precedent, there’s not a single synthesized instrument in the song. The second shock is the sheer rawness of Madonna’s vocal performance - where almost any other singer would have scaled typically balladic heights, she’s restrained, but resolute and infinitely more honest for it.

Whilst Promise to Try, a pledge to her younger self, was about the pain of her mother’s death, Oh Father appears to open with the same childhood anguish, but from her father’s side. Coming from a 30-year-old Madonna, “you never loved me” sounds like an accusation, and the chorus virtually an account of child abuse - but is it really? Or is the act of blaming her father merely “what a child will believe”? The girlish, pure backing vocals in the chorus feel like a memory - nothing like the wounded vibrato of Madonna’s lead vocals.

On the other hand, the second verse casts some of the blame on herself. In 1985, she told Time, “I have a lot of feelings of love and warmth for her but sometimes I think I tortured her. I think little kids do that to people who are really good to them. They can’t believe they’re not getting yelled at or something so they taunt you. I really taunted my mother.”

There is a common story that Madonna Fortin Ciccone, exhausted from her treatment for breast cancer, sat down to take a break from looking after her kids - and a five-year-old Madonna Louise Ciccone climbed on top of her, hitting her, demanding attention. But her mother lacked the strength - “I was so little and I put my arms around her and I could feel her body underneath me sobbing and I felt like she was the child.” No doubt the young Madonna had feelings of guilt, however unfounded, over her mother’s death. But on the other hand, the way “Oh Father I have sinned” prefaces the second chorus, it becomes as much an indictment of Catholicism, and perhaps God himself, for taking her mother away prematurely. “I never felt so good about myself” - but was that God’s fault, or her own, or her father’s?

As honest as the song may be, there is not much literal truth to be found here. Madonna has never claimed her father intentionally abused her, physically or mentally, but as for the metaphorical? The art ultimately exists for its own sake - it doesn’t have to be literally true to be honest or biographical.

Interestingly, the Like a Prayer album booklet prefaces those two lines with an “if” that’s not on the recording. It’s a minor detail, but left in, it changes Madonna’s faith in her father’s good intentions into a questioning cynicism that would’ve been at odds with the song’s more reconciliatory conclusion.

That “maybe” is as cautious as forgiveness gets - she knows it’s true, but she doesn’t quite feel it in her heart yet. Essentially, Oh Father concludes with the understanding that the trauma of her mother’s death, subsequent guilt and her repressive Catholic upbringing weren’t truly her father’s fault - in a way, all three stemmed from God himself, a higher Father. But she never quite points the finger; and when she finally sings the last choruses in full, she knows “you can’t hurt me now”. It’s a bitter Madonna, but one who’s now at peace.

As with most of Madonna’s more personal, biographical efforts, Oh Father has a fairly literal visual interpretation of the music. The black-and-white, wintry look draws inspiration from the grand, archetypal cinema of Citizen Kane - and more than any of her other videos, there’s something truly cinematic about the moody low-key lighting. There’s an incredible attention to detail - from her mother’s death and funeral (the sewn lips representing her silence, a true story), to having three separate actors with uncanny resemblances to her father Silvio Ciccone, to recurring themes like the scattered pearl necklace. Most remarkable is how it blurs the past and present - the adult Madonna comfortably observes from the fringes of her childhood memories, and vice-versa towards the end, where she and her father cast the shadows of their arguing younger selves. Most significantly, she seems to take on the spirit of her own mother, the older Madonna, at the bedside of her younger, 20-something father. She delivers her final forgiveness with a kiss, whilst her present-day bond with her father goes unspoken - they simply share the memory and love of her mother. This was somewhat true of their real-life relationship as well - when asked by MTV’s Kurt Loder if her father had seen the video, Madonna replied, “To tell you the truth, I don’t know if he’s seen it. I’m kind of afraid to call him up and ask him.”

Oh Father is absolutely one of Madonna’s greatest works, and crucial to understanding her psyche both as an artist and a person. But despite all this, it seems to warrant little mention in present recaps of her career. Celebration seems content to portray most of her career as a party, defining her greatest songs as hits more than anything else. But why wasn’t it even on the supposedly completionist DVD? Really, the Madonna of today can do whatever she likes - unlike the Madonna who was once compelled to prove herself as a serious artist. It’s a shame that Oh Father doesn’t have a place in the canon of her body of work, because it certainly deserves it - its exclusion is selling herself short on both artistic and personal levels.

Albums: Like a Prayer (1989), The Immaculate Collection (1990), Celebration (2009)
Songwriters/producers: Madonna/Patrick Leonard

As an album, Like a Prayer is often lauded for its incredible diversity - but rarely is it remarked upon how plain odd its sequencing is. This is an album that delights in its jarring transitions - the way it goes from the divorce and domestic violence of Till Death Do Us Part to the sunny, entirely optimistic Cherish within only three songs would be utterly baffling if they weren’t pulled off so well. To call Like a Prayer Madonna’s “divorce” or “religious” album, as it is so commonly labelled, would be to ignore songs like Cherish - which, however contradictory, are a big part of Like a Prayer as a whole. Instead, call it her most personal album - one where Madonna shows her true complexity as an artist by portraying practically the entire range of human emotion.

Cherish is certainly the most outright pop song on Like a Prayer, but its origins lie in the girl-group sound Madonna had been pursuing since Like a Virgin. But where Shoo-Bee-Doo felt cliché, True Blue simply shone - and Cherish takes the style to its final conclusion and greatest heights. It’s the feelings of a woman shedding all the baggage of past failures and relationships for a pure, instinctive infatuation - but one that’s never blind to the need for something lasting, “more than just romance”. Though songs like Vogue and Ray of Light still had the feeling of boundless elation that made so many of her ’80s singles great, such statements of optimism as Cherish were something she’d literally never again attempt. Madonna’s recent Rolling Stone interview shed some light on her present feelings:

Fair enough - one can’t blame her for seeing their optimism as her own youthful naïveté. But she still sings Into the Groove, reinterpreting it mercilessly on the Sticky & Sweet Tour, and Cherish makes for a brilliant transition to the title track on Celebration. Whatever her personal feelings, it’s hardly fanservice when the songs themselves are that great.

Herb Ritts, the man responsible for the True Blue album cover, along with many of Madonna’s most iconic images, had at some point actually become a punchline for photographic style over substance.

But just as Madonna’s huge mainstream appeal doesn’t imply a lack of artistry, nor did the sheer glamour of Ritts’ photography detract from the incredibly evocative nature of his portraits. Though he had no experience in film, Madonna somehow roped him into directing her video for Cherish, and the results are one of the purest distillations of his signature style. Despite, or perhaps because she wears a swimsuit only revealing by 1920s standards, Madonna’s toned figure is as sexy as ever as she rolls around in sand and frolics with mermen. And though shot entirely by Ritts himself on a handheld camera in freezing weather, the blue-tinged monochrome of the beach is nothing but bright and sunny. With none of the extended metaphors of her last two videos, Cherish is just an incredible visual spectacle, but it does it so well that it’s nearly faultless.

(the making of Cherish, from an interview with Herb Ritts - R.I.P.)

Albums: Like a Prayer (1989), The Immaculate Collection (1990), Celebration (2009)
Songwriters/producers: Madonna/Stephen Bray

N.W.A., the seminal hip-hop act and pioneers of gangsta rap outrage, have a lot more in common with Madonna than you’d think… that is, besides both having classic 1989 singles called Express Yourself. When N.W.A.’s version called for rappers not to hold back, to forget the censorship pop music demands, they might as well have been rapping about Madonna - for who else could successfully funnel counterculture and controversy into the confines of a #1 single? Her take on Express Yourself is an insistent denial to anyone who ever took her mock-Material Girl image at face value, and one of the clearest, most inclusive feminist messages ever put to song.

Madonna’s brand of sex-positive feminism is true equality in that it acknowledges men - with no possible accusations of man-hating, any objections can be blamed on the insecurities of domineering macho types. Though she uses every bit of her iconic status to call on women to “make him express himself”, the song’s title, Express Yourself, is also an appeal to male listeners to prove they deserve the women they’re with. “Long-stemmed roses are the way to your heart, but he needs to start with your head” - not the other-way-around double entendre, for material gifts are one thing, but intelligence and empathy go a long way. It perfectly reinforces Madonna’s oft-misinterpreted sexual politics - firstly, that to be desired is empowering, and secondly, that a visible, free-spirited sexuality can be for one’s own sake, and not imply a come-on to any man that’ll have her. As she’d soon whisper on Justify My Love, “poor is the man whose pleasures depend on the permission of another” - and of course, the same goes for women. The heart of the song isn’t a series of demands towards men, but a celebration of womanhood - beautiful, empowered, self-sufficient, but partial to a partner who really can “lift you to your higher ground”… mutually.

Madonna’s original roots may have been in disco, an essentially black form of music, but Express Yourself turns time back to the late ’60s, a perfectly authentic tribute to soul if there ever was one. The album version’s horn section, effortlessly bouncy bassline and generous backing vocals make it a Respect-level anthem for the 1980s, with the difference that Express Yourself (despite having some of Madonna’s strongest vocals) could actually be sung along to. However, Shep Pettibone’s 7” remix was released as the single and video, and included on both The Immaculate Collection and Celebration. With most of the band replaced with synthesisers and house beats - the kind that’d be explored more fully the subsequent year on Vogue - it lacks the album version’s depth, though it’s a little more danceable, more commercial and still excellent nonetheless.

The video for Express Yourself is really the start of Madonna’s Blond Ambition phase - the queen taking place on her throne, revelling in the attention, but always shining the light back onto her subjects. Ever since Material Girl, her ability to pay tribute to the icons before her time and not steal from, but reinterpret them, was much of what cemented her own timelessness. Express Yourself effectively takes the surreal industrial imagery of Fritz Lang’s classic film Metropolis and spins it into something else altogether. It puts Madonna at the top, the epitome of the successful career woman - stunningly beautiful, totally feminine, but also able to dominate in traditionally male roles - as shown by the contrast between her usually curvy appearance and that tense dance in an oversized tuxedo. She oversees a bunch of almost-as-beautiful male factory workers, but while they work, exercise and engage in the traditional competitive male form of conflict resolution - fighting - one man aspires to a little more. Instead of taking part in the macho cockfighting, he looks after Madonna’s adventurous black cat, giving him the balls to take the elevator straight to her bedroom and seduce her. The way I see it, his disregarding of “traditional” masculinity, and his empathy symbolised by the cat are proof of his worth as a lover, a partner - and perhaps Madonna’s crawling to lap up a bowl of milk shows that she is the cat? Throw into the mix a creepy suited observer (her husband? the boss?) and his wind-up horn section and you have a work of art every bit as metaphorically complex as Like a Prayer. And you have to give her credit for gender equality, as always - rather than reducing the female sexuality on show, getting half-naked male models to work out on MTV was a pretty effective way to even out all the eye candy on display. A classic in every sense of the word.