Madonna strikes me as a cold, dour bird - someone who takes herself much too seriously and never appears to genuinely enjoy anything. At the beginning of her career, this wasn't really an issue. Never more than an average singer or dancer, her gimmick was her originality and genuine lack of concern about what others thought. She did, said, sang and wore what she wanted and as a result launched multiple trends, becoming a true cultural icon of the '80s and early '90s. Her music was fun, if she wasn't, and she was at least interesting.
But the years have not been kind to the woman, frankly. Oh sure, she's filthy wealthy, looks good and is bendy as fuck but there's been more than a whiff of desperation about her in the last decade, a chapter I'd title "Trying Too Hard". I'm not saying when a woman reaches a certain age, she should bundle herself inside never to be seen again, but I am saying that it's probably unnecessary for said woman to roll around the floor in a pink, satin leotard. Also unnecessary: American Pie covers, children's books, movies about British royalty and - I can't stress this enough - rapping.
So while I've largely rolled my eyes at her recent body of work, I can't deny the allure of some of her earlier "songs:
- "Borderline": In this winsome little tune from her self-titled debut album, Madonna winningly displays both strength and vulnerability, imploring her partner to treat her right or let her go. Her singing is restrained and serious, displaying a certain frailty backed by growing resolve. There are also shades of Motown here - I can imagine this being sung by The Supremes or Tammi Terrell 20 years earlier with a few tweaks.
- "Live to Tell": This melancholy ballad was written for the soundtrack of one of then-husband Sean Penn's movies. I can't remember what it was called, nor can I be arsed to look it up. The clips in the song's video look like it might be Footloose, but then Christopher Walken shows up and I know he wasn't in that, but wouldn't it have been two-thousand times more awesome if he'd played the Kevin Bacon character and it was about tap dancing? Anyway, this is a very minimalist, quiet song with something just a little bit beautiful about it. I like the lost, lonely feeling it conveys.
- "Buenos Aires": A choice with a Broadway twist, from her surprisingly solid turn in the movie version of Evita. Madonna belts this one out with the determined optimism of a young Eva Peron arriving in the Argentinian capital with a plan to make the city her own. Kudos to her for making it sound exciting even if meant having to sleep with Picasso-faced Jimmy Nail to get there.
- "Bedtime Story": A song that makes the list more due to its writer than its singer, this is a trance-influenced song written by Bjork that still sounds fresh and alluring today, despite being nearly 20-years old. Both the song and its stunning, surrealistic video illustrate exactly what I think it must be like inside Bjork's head at any given moment. Madonna sings "Today is the last day that I'm using words. They've gone out, lost their meaning, don't function anymore", and I can totally envision Bjork waking up one morning deciding only to communicate through facial tics and pixies. Madonna chose her collaborators wisely on this one and does a good job of remaining restrained in her performance, letting the strong lyrics and languorous music seduce the listener.
- "Ray of Light": Arguably Madonna's last great hit, this song is Bedtime Story on a near-fatal sugar high. With echoes of techno and trance, it speeds along at a frenetic pace, flinging you through space and time. It's joyous, exciting, mature and unencumbered by painful attempts at being terribly trendy and relevant. And it's a hint at what Madonna could do if she stopped worrying about her image and concentrated on enjoying the music.