Albums: Barcelona Gold (1992), Something to Remember (1995)
Songwriters/producers: Madonna/Shep Pettibone

The main reason why Madonna’s non-album tracks are so forgettable is, simply, because her instinct for self-editing is generally so spot-on. Naturally, there are plenty of examples from periods where she was overflowing with great material - but for each Into the Groove or Crazy for You, there are ten Supernaturals or It’s So Cools. Of course, good songwriting is more about an artist’s highs than the consistency of their every bootleg-recorded breath; no one is that good. So in retrospect, an offcut from Erotica - beloved by some, yet deeply inconsistent - from the soundtrack to a women’s baseball film doesn’t sound too promising. But at the time, as her first new material in over a year, This Used to Be My Playground became her tenth number one on the Billboard charts.

Despite being one of the last songs recorded during the Erotica sessions, This Used to Be My Playground stylistically had nothing to do with the then-upcoming album; its MOR balladry instead foreshadowed Madonna’s Something to Remember era three years later. Strangely, likely due to issues Warner had with Columbia/Sony distributing the film, its initial release was not on the soundtrack to A League of Their Own, but the entirely forgotten Olympic-inspired Barcelona Gold compilation.

Though Madonna’s previous musings on innocence in Live to Tell and Oh Father expressed a dark, yet incredibly complex range of emotions, This Used to Be My Playground simply wallows in the past. It’s not necessarily more sentimental than heartfelt, but there’s no sense of resolution, none of her trademark determination - just grey skies as far as the eye can see. As an artist who’s always steadfastly refused to look back or mythologise her own achievements, the self-indulgent nostalgia of “don’t hold on to the past/well that’s too much to ask” is thoroughly unconvincing. Shep Pettibone’s slightly plodding production - complete with stock pop-ballad strings and a synth-glockenspiel intro - only serves to push the song into borderline schmaltzy territory; something Madonna should always have been above. But she had much better songs up her sleeve - when literally half her singles that decade were to be ballads, she damn well needed them.

Director: Alek Keshishian

The video is nothing special - someone flips through a photo album as Madonna sings from the various pictures inside. Everyone involved is on autopilot; though the video obviously strives to depict snippets of memories, the scrapbook motif makes the budget look low, and Madonna static.

For once, Madonna’s cinematic ambitions here far outweigh her musical interpretation; A League of Their Own is, simply, a great film. Its solid, witty screenplay was exactly what Madonna’s last four major efforts lacked - and she held her own amongst the ensemble cast, her performance and the film her most critically acclaimed since Desperately Seeking Susan.

Given the prefeminist World War II setting, it’s easy to see why Madonna was eager for the part - with the men away and a female baseball league in demand, it was the perfect opportunity for women to express their talent in a traditionally male role whilst, most importantly, remaining themselves. Despite the patronising nature of making women’s baseball appealing, from etiquette classes to their impractical, skimpy uniforms, the players impress even where they don’t succeed. Dramatised or not, the film forces the audience to admit that the women of the real-life All-American Girls Professional Baseball League were, though not always intentionally, true pioneers - both athletic and feminist.

“What if at a key moment in the game, my uniform bursts open, and oops - my bosoms come flying out? That might draw a crowd, right?”
“You think there are men in this country who ain’t seen your bosoms?”
- Mae Mordabito (Madonna) and Doris Murphy (Rosie O’Donnell), not entirely acting

Madonna is cast perfectly as “All the Way” Mae Mordabito, something of an exaggeratedly promiscuous, 1940s baseballer version of herself - alongside Rosie O’Donnell, their brash charisma is a highlight of the first half of the film. But just as importantly, she knows her place despite her top billing, downplaying her role to make way for a fierce Geena Davis and a wonderfully over-the-top, immediately pre-fame Tom Hanks as manager. Director Penny Marshall offsets the action by bookending it with scenes of a fifty-years-later Hall of Fame reunion - though often derided for their sentimentalism, there’s nonetheless a truth in athletes (or anyone, really) wanting to relive their glory years. But as a now-and-then team picture fades into the credits over the strains of This Used to Be My Playground, one can’t help but feel the film ends on the wrong note. As with most sports movies, the point should be the glory of being, triumphing in the moment - but without the nuance of the past two hours, the final impression portrays it as a nostalgic period piece; saddened in the present, hence not quite uplifting enough. You’d think there’d be no one better than the real-life Madonna Ciccone to teach the value of that lesson.

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: True Blue (1986), The Immaculate Collection (1990), Something to Remember (1995), The Confessions Tour (2007), Celebration (2009)
Songwriters/producers: Madonna/Patrick Leonard

Pop has always been seen as music made for the youth, by the relative youth. Whilst the popstar of the moment can get by on exuberance alone, as they grow older, the sheer difficulty of exuding an expected maturity in an art form largely concerned with instant gratification only gets worse. Whereas AC/DC can churn out the same album for 30 years, society saves its harshest ageism for the aging female popstar for doing the same.

Madonna at 51 has now been fighting that battle for literally decades - but once, in 1986, she decided to jump the gun before the weight of her teenage wannabe following became too heavy a burden. Live to Tell, though immediately different from any other Madonna single, is an entirely natural transition - she never feels like she’s out to prove herself. Even though she’s not in a position of power for once - the lyrics being about escape from some form of sexual or domestic abuse - the strength of her determination is, as always, what gives the song life.

Where the closest reference point, her Love Don’t Live Here Anymore cover (to be reviewed during Something to Remember) on Like a Virgin, builds to an anguished peak, Live to Tell is more emotionally restrained and cinematic - but just as dark. Its brooding, mid-tempo nature may make it the least instant of Madonna’s ’80s singles, but also one of the most rewarding.

The music video was likely the public’s first glimpse into the new Madonna on her own terms - away from the constant media obsession following her recent marriage to Sean Penn. Nonetheless, there’s still a connection - Live to Tell having been originally written by Patrick Leonard for a different film, then recorded by Madonna for At Close Range, starring none other than Sean Penn. The video alternates clips from the film - not having seen it, I can’t comment on the song’s relevance - with shots of a very plain-looking (but undeniably beautiful), emotive Madonna. She wouldn’t stand out from a crowd of average people - but she would stick out in a crowd of Madonna wannabes, and in that respect, her first of many image makeovers succeeded perfectly.

The performance of Live to Tell on the Confessions Tour was likely Madonna’s last real controversy - supposedly for drawing messianic comparisons by singing it atop a giant disco cross, wearing a crown of thorns. In typical kneejerk fashion, those doing the condemning had likely heard of, but not seen the performance itself. Musically, the slightly modernised arrangement with the classical organ works wonders, and Madonna sounds perfectly in her element - the melody is an ideal fit for her current tone and vocal range. Visually, it’s nothing if not fascinating; a counter ticks from zero to 12 million - a measure of the number of children orphaned as a result of AIDS, with images interspersed - and stops abruptly at the song’s bridge, when Madonna comes down from the cross.

My secular, thought-out interpretation is this: firstly, Madonna sings both for and from the perspective of the orphans. Inner strength and determination in harsh times - exactly what the song is about, and one thing they need. Secondly, and most importantly to the perception of the performance, she comes down from the cross. Though she may attempt to help the situation, it’s not her burden to bear - at least not alone. As she gestures to the crowd, takes off the crown of thorns and lays down, the Raising Malawi and Clinton Foundation websites flash onscreen. The message - to extend both solidarity and support, that they’ll make it through - should be clear (though honestly, she says it better herself).

Blasphemy? Hah - for being one of few popstars able to encourage compassion and charity without resorting to preaching or grandstanding, Madonna deserves nothing but praise.

Albums: Vision Quest (1985), The Immaculate Collection (1990), Something to Remember (1995), Celebration (2009)
Songwriters: John Bettis/Jon Lind
Producer: John “Jellybean” Benitez

Madonna’s one and only power ballad, and thankfully it’s pure class. The first of her many great soundtrack contributions, it was written for the film Vision Quest and in fact recorded before the Like a Virgin album despite its subsequent release. Though there’s a thin line between doe-eyed infatuation and sappiness, Crazy for You is well-written enough to envelop, but never quite overwhelm the senses. Madonna’s vocals (apparently recorded in one take - not sure how that works with the double-tracking) are, for the first time, spectacular - as she’d often do later on, the smoky verses build into a powerful, nearly belted release of a chorus. It’s the ’80s ballad done to perfection, but more representative of pop in general than her later, far more adventurous efforts.

(above at 0:57 is the song’s occurrence in the film; the music video compiled of clips from the movie is here)

Vision Quest isn’t too bad at all - kind of a romance/coming-of-age film via high school wrestling. With or without the various wrestling scenes, it’s one of the most bizarrely, almost obliviously homoerotic films I’ve ever seen - but thankfully Linda Fiorentino’s pure attitude balances out Matthew Modine’s incredible awkwardness. Madonna plays a nightclub singer, performing Gambler and Crazy for You - and in the film’s setting, the song is absolutely perfect, a vision of intimacy in a crowded room. She’s charismatic as usual, but thankfully doesn’t try to steal the show. The version of the song used in the film is for some reason totally different to every other issue; a tone higher (on my $5 DVD copy), with a rawer sound more befitting the live band vibe. Madonna’s vocals, which may even have been recorded live and not mimed, have little of the familiar, powerful double-tracking; instead she slides into the high notes almost timidly. At the risk of retconning her inability to replicate them live, one could say the song’s reserved performance in the middle of the film blossoms into its more confident, final version as the movie’s theme.

Though a young Madonna filmed and recorded her appearance to piggyback on Vision Quest’s publicity, the tables had already turned by the time of its release - the universal nature of Crazy for You only added to the momentum.