You may have heard that this is the 20th year of ALANILAGAN.com, and as such I’m going to start culling a few ‘Top Twenty’ lists from the archives in celebration of such a milestone. (Who knows if I might make to another?) We’ll begin with one that is close to my musical heart: the Top Twenty Madonna Timelines. (These are not in any strict order, as it’s too difficult to rank that, they are just twenty notable timelines.)
The Madonna Timeline has been a regular installment here wherein I dissect a specific Madonna song (chosen randomly by the ‘Shuffle’ feature) and go into whatever memories or background I have of the song, when it was released, and/or what it has come to mean to me over the years. For a long time, I could date my life based on what Madonna era was happening, but failing memory and lack of indelible career moments have largely left that in the past. Here’s a reminder of some of my favorites.
1. Drowned World/Substitute for Love ~ This is my favorite Madonna song (with the caveat that such a preposterous proclamation is always subject to change – but this one has stayed at the top of my list since it came out in 1998, and as much as I adore her I don’t see Madonna topping this one anytime sooner or later). The opening track of her best album to date (the miraculous ‘Ray of Light’) this song ushered in one of the greatest Madonna eras ever. It was once again about the music, and this music came with layered nuance, lyrical poignance, and introspective grace. It was an emotional reckoning, highlighted by this compelling track, which seduces the listener with a calm and languid beginning then ruminates on the price of love and fame and the search for something more before culminating in one of the most powerful bridges she has ever written.
2. Vogue ~ Madonna has always been about fun and glamour, and nowhere is that more evident than in her classic anthem ‘Vogue’. From the opening command of ‘Strike a pose!’ to the quasi-rap litany of Hollywood royalty, this is Madonna at the crux of fabulous and campy in an ode and an invitation to the gay balls of the late 80’s. It also inspired a major timeline sprinkled with Oscar Wilde quotes and gay memories galore.
3. Like A Prayer ~ The rarefied upper-echelon of Madonna’s catalog contains many iconic moments and the crowning jewel of her musical oeuvre has to be ‘Like A Prayer’. For substance, style, and transformative musical transcendence, this remains Madonna’s most majestic move, and it has endured for decades with good reason.
4. Erotica ~ Sex and sin and seduction, oh my! A turning point in Madonna’s career formed a valuable and necessary life-lesson for me, laying the groundwork for my own creative expression.
5. Turn Up the Radio ~ Losing oneself in a pop song is one of Madonna’s most enduring hat-tricks, and a large reason why some of us have never been able to quit her. ‘Turn Up the Radio’ starts off as a stellar slice of escapist pop music, until you realize by the bridge she is desperately doing all that she can to simply survive (“We gotta have fun, if that’s all that we do”).
6. Rain ~ Forging the heart of the gorgeously-icy ‘Erotica’ album, ‘Rain’ was part of a pivotal moment in my life – and may have actually saved it.
7. Rebel Heart ~ At this stage in her career and life, Madonna has nothing left to prove, but an air of defiance imbues the title track of the under-appreciated-if-chaotic ‘Rebel Heart’ album. It’s a bit of a look-back and reassessment of “all the things I did just to be seen” while refusing to be anything other than the rebel she has always embodied.
8. Crazy For You ~ One of my very first crushes forms the narrative portion of this Madonna Timeline, and for that reason it holds a special place in my heart.
9. Secret ~ The Madonna song that will forever be linked with the memory of the first man I ever kissed, ‘Secret’ is heartbreaking on a personal level, and healing in the same way.
10. You Must Love Me ~ Though I was semi-stalking a young man at the time this song came out, ‘You Must Love Me’ eventually became the command that came true, as the object of my affection way back then ended up becoming a lifelong friend.
11. Music ~ When it comes to fun, nobody does a better bop than Madonna. From ‘Holiday’ to ‘Spotlight’ to her millennium-opener ‘Music’, she knows how to craft a catchy and infectious tune. Coupled with the first few months of dating Andy, this song informs one of the happiest times in my life.
12. Express Yourself ~ Another moment in Madonna history is also one of the most self-empowering songs ever written, and this take-charge anthem is a potent blast of pop perfection (cue the horny horn break).
13. Ray of Light ~ Exploding out of the spring and summer of 1998, the lead track to Madonna’s greatest album ‘Ray of Light’ is a roaring revelation of celebratory abandon and realization – the zenith of Madonna’s dance-pop evolution, even if she had no hand in actually writing the song. The timeline is always a fun memory, as it brings me back to a night in Boston when, fueled by a cocktail of something called ‘Liquid Cocaine’, I sped through Copley Square on roller-blades with a long black cloak flowing in my wake.
14. Messiah ~ Despite her ‘Something to Remember’ collection, Madonna has never truly been appreciated for her ballads, which is criminal, as they form the compelling contrast and anchors of so many of her albums. This selection from the somewhat-messy ‘Rebel Heart’ opus echoes other brilliant balladry such as ‘Falling Free’, ‘Promise to Try’, ‘I’ll Remember’ and ‘I Want You’.
15. True Blue – An ode to old-fashioned romance and sweet, hopeful innocence, this frothy confection of ear candy goes down easy and rekindles a simpler time in life.
16. Live to Tell ~ The best songs of Madonna transcend the limitations of pop music, allowing multiple readings and layers of interpretation. ‘Live to Tell’ hints at secrets and betrayals, survival and destruction, and is one of Madonna’s most serious and powerful ballads.
17. Secret Garden ~ Closing out the sexual kaleidoscope of ‘Erotica’, this glorious glimpse of a metaphorical musical garden found flowering and fruition and little to nothing to do with fucking. A precursor to cocky clickbait.
18. You’ll See ~ Turning romantic tragedy to independent triumph, ‘You’ll See’ was pegged as the ‘I Will Survive’ of its day, and it came at a time when my own romantic adventures were just beginning.
19. Survival – Opening her deceptively-soft-focused ‘Bedtime Stories’ album (one of the most unexpectedly-pivotal albums in her career, lowering expectations as it repositioned her as an artist who would endure rather than burn-out in a blaze of glory) this track and timeline found both Madonna and myself in a fascinating state of flux.
20. Material Girl ~ Where it all began for me.
