Popmatters published its list of the top fifteen Madonna songs. I have more problems with the terms of evaluation than the selections. What is “personal”? What is “poetic” other than that “the lyrics are pretty”?
Mine:
15. Sky Fits Heaven (Ray of Light, 1998). Subterranean beats meet Madonna’s lower register. The only time in song — or in real life — her karmic ruminations are worth a damn. Terrific key change in the chorus too. Whoever thought of inserting a piano gets $10.
14. Sorry (Confessions on a Dance Floor, 2005). She’s taken flack for pedestrian lyrics in the last fifteen years, but when they bait a production this relentless it’s a mood point.
13. Gambler (Vision Quest soundtrack, 1995). Purest rock-disco, with a grab-you-by-the-lapels vocal and one of her best lines: “You’re just jealous cuz you can’t be me” – in 1985, before she was, you know, Madonna. Trivia: her last solo songwriting credit.
12. Bedtime Stories (Bedtime Stories, 1994). Aurally “Sky Fits Heaven” is the friskier update of this insinuating piece of Bjork-penned throb-beat.
11. Words (Erotica, 1992). “How ’bout the faux-Arab electro on “Words”? And aren’t the techno effects all nice and cheesy-futuristic?” – Robert Christgau.
10. Angel (Like a Virgin, 1985). The first hit on which Madonna experimented with a lower register, an experiment broken only when her voice cracks into major keys on the line, “In disguise, I can SEE it in your E-Y-E-ES!!” Also: the Nile Rodgers band sounds as on-the-one and inventive as Bernard Edwards’ in Power Station does not.
9. Where’s The Party (Dub Version) (You Can Dance, 1987). The essence of thunderous electro-salsa.
8. Burning Up (Madonna, 1983). Check out the demo. Stephen Bray: “Looking back, it seems we nailed a ‘Joan Jett’ sitting in with ‘New Order’ kind of sound.”
7. Crazy For You (Like a Virgin, 1985). We know the feeling of watching the other guy dancing with someone else and not even knowing you’re alive.
6. Vogue (I’m Breathless, 1990). Like Bowie discovering Philly soul in ’75, Madonna goes house in ’90, at home with Betty Boo, Black Box, Adamski, etc yet more imperious and weirder than ever. You can’t imagine how educational it was for a fifteen year old to hear Greta Garbo and Rita Hayworth’s name in a #1 pop song, or reducing ten years of listening to pop to a couple of lines: “Strike a pose/There’s nothing to it.”
5. Deeper and Deeper (Erotica, 1992). See #6, darkened by thunderclouds of rue.
4. Live to Tell (True Blue, 1986). The key here is how well Madonna’s vocals harmonize with Patrick Leonard’s keyboards, how skillfully they navigate the air pockets between those synths and the drums. Then there’s the middle eight.
3. Into The Groove (You Can Dance; released in 1985). See #7 — a dream fulfilled. The essence of joy.
2. Like a Prayer (Like a Prayer, 1989). Synth bass and real bass collude in taking Madonna to the river. As she’s dragged screaming, taunted by a gospel choir, she shares the ultimate disco koan: “Life is a mystery/Everyone must stand alone.”
1. Open Your Heart (True Blue, 1986). Can you take lessons to sound this euphoric? For all my distrust of “positivity” here’s one track that makes me feel like I can do anything.
Humanizing The Vacuum 
Nice one. Here’s mine, not in order of preference but starting with duplicates from your own list. .
Live to Tell
Into the Groove
Like a Prayer
Open Your Heart
+
Holiday
Borderline
Lucky Star (I think I’m saying her first album is still maybe her best — highest ratio of great singles, for sure… “Burning Up” is definitely a contender)
Drowned World/Substitute for Love
Bad Girl
Oh Father
Ray of Light
Hung Up
Beautiful Stranger
Keep it Together (Shep Pettibone 12″ remix)
Nobody’s Perfect
I like your list, especially the inclusion of “Keep it Together,” which along with “Causing a Commotion” is her least anthologized, most forgotten (by her) major single. I’m surprised by “Drowned World” – I’d have thought the lyrics were too, well, didactic for your taste.
“Drowned World” is a song I loved musically for so long I only noticed a) the didactic words and b) her incredibly mannered (almost to the point of distraction) phrasing a few years ago! (Not even sure what prompted me to suddenly hear it that way — some dismissal I read somewhere, maybe on ILM… she does sound kind of ridiculous in it.) I still think the production, the arrangement (William Orbit’s stunning little drum machine flourishes), and the melodies make it one of her most gorgeous and heartbreaking creations.
I love the contexts you place “Vogue” in, and I’ve played the shit out of that song as a DJ (though it didn’t prove to have major staying power, like “Holiday,” “Into the Groove,” or “Like a Prayer” in that regard), but for some reason, I’ve just never felt that one. Something about the chilliness of the beat always prevented me from loving it… but Philly soul Bowie is a ridiculously great comparison. (And yet… I love much of Young Americans!)