Madonna: Looking Back

The release of a new Madonna album is always a significant happening in the pop music world, for Madonna is the greatest living pop musician. Yes, others have had more #1 hits (Mariah Carey in the US, and, cringe, Westlife in the UK), sold more albums (Michael Jackson), had longer careers (Elton John), and won more Grammies (she's won so few), but nobody on balance has achieved these milestones and so much more in the way that she has (other than the Beatles and Elvis, but I did qualify my statement with "living"). Her influence is omnipresent, heard in the hits of Gwen Stefani, Britney Spears, and others, seen in countless music videos, and informs the image of every female pop star looking to copy her successful blend of sex, mystery, smarts, and consistency.

Confessions on a Dancefloor is Madonna's 11th album (yes that counts I'm Breathless, which was not the soundtrack to Dick Tracy, and no, it does not count GHV2 or The Imacculate Collection, which were compilations, not albums). As such, I felt it proper on the eve of its release to take a moment to look back upon her career thus far. The challenge I put to myself: Selection the 10 singles that best enscapsulate Madonna's career. I do not posit these songs are her greatest hits or my favorite songs, but rather 10 markers of the breadth of her catalogue, 5 songs from the '80s, 4 from the '90s, and 1 from the '00s.

1. "Holiday," from Madonna (1984)

By the time of its release, Madonna had already been making waves at dance clubs, but Holiday introduced her to masses, giving her the first of many top 40 hits. Not the biggest hit from Madonna, but certainly the most memorable. It's won a special place in fans hearts, and apparently Madonna's too, as it is the only song she has included in the setlist of every tour.

2. "Like a Virgin," from Like a Virgin (1984)

"Holiday" made her a star, but "Like a Virgin" made her a worldwide superstar, and marks the beginning of the important incorporation of image into her work, a process repeated by every major star since. With the video, the album cover photo, the press appearances, the blatant display of sexuality, and the attitude, Madonna began not just selling her music, but selling herself.

3. "Into the Groove," from Desperately Seeking Susan soundtrack (1985)

Like a Virgin was more a pure pop album than her clubby debut, Madonna, so "Into the Groove" was a return to her club roots, which showed to her now swelling fanbase weaned on Virgin that disco may be dead, but you can still dance. Interestingly, "Into the Groove" is her biggest hit that never was. Everyone knows it. It still gets a lot of radio airplay. But, at least in the US, it was never a single (it was in the UK, and a big one-- weeks #1).

4. "Papa Don't Preach," from True Blue (1986)

True Blue proved that Like a Virgin wasn't a flash in the pan, and that Madonna was here to stay. The album was overall more consistent, and "Papa Don't Preach" was its shining star, a lushly produced, more mature, somewhat dark number about a troubled (pregnant) young man seeking the support (not advice) of her father, as she is determined to make the relationship work and keep the baby. It also shows Madonna's strategy of embracing controversy as part of her work, as the song drew fire from both the left (because it sounded somewhat pro-life) and the right (she was, afterall, having the baby out of wedlock).

5. "Like a Prayer," from Like a Prayer (1989)

Up to Like a Prayer, Madonna was making catchy, well-crafted pop music, but it lacked an essential ingredient--the personal. Like a Prayer changed that and began the exploration of several personal themes that would repeat themselves throughout her work: her deceased mother, her evolving relationship with her father (and family in general), her faith and relationship with god, and her romantic attachments. "Like a Prayer" was the album's opening and strongest moment, blending imagery of religion and romance (how taboo), laced with choirs, organs, and electric guitars. The controversial video, of course, was notorious for scaring off sponsor Pepsi.

6. "Vogue," from I'm Breathless (1990)

I count 1990 as the peak of Madonna's career and the best example of her ability to create synergy--one of her most important star-making traits. In 1990, everything Madonna touched was gold, and everything tied together, cross-marketing the entire neat package. Her image, the blond vamp of the '20s, remains her most iconic image, best showcased by "Vogue," the brilliant modern dance single (and video) that pays tribute to past icons of dance and showbiz. The same year, she co-starred in Dick Tracy, one of her few films to escape scathing reviews. It was the perfect vehicle for her to maintain the '20s vamp image (she basically played herself in the movie), win Hollywood's hottest guy (Warren Beatty), and upon which to base her own album of '20s-inspired songs. The year also saw her hottest, most theatrical tour to date, Blonde Ambition, and was capped by the release of The Immaculate Collection, the definitive model of how to a greatest hits collection right.

7. "Erotica," from Erotica (1992)

If 1990 was her highest point, then 1992 was her lowest. All the momentum she built just two years earlier came crashing down with another broad effort to create synergy, but one the public was not ready for. This time the image was sex, raw and pure. First came the album. Erotica, produced solely by Shep Pettibone, was concept album with dark bent full of cutting-edge dance music and sexual energy, that was underrated and quickly overshadowed by what came next: the book. Madonna published her first book, Sex, a photo-fantasy of sex and sadomasochism, where she assumed the identity of Dita, that was literally a disaster (the spiral bound product fell apart easily) and earned her scads of negative press. Finally, there was the movie, Body of Evidence, where she played a woman accused of murder through sadomasochistic sex, which earned poor reviews and more bad press. "Erotica," was the album's first single, a cold club thumper featuring Madonna purring as Dita, owing more than a little resemblance to an earlier hit, "Justify My Love."

8. "Take a Bow," from Bedtime Stories (1994)

So, time for some damage control. Madonna followed Erotica with Bedtime Stories, which by the title sounds like more of the same, but was actually Madonna playing it safe for the first time. Instead of 1 producer, she pulled in a whole entourage of the most popular R&B/Pop producers. "Take a Bow," produced by Babyface, gave Madonna one her biggest hits ever in the US (but strangely one of her smallest in the UK) and topped the Billboard Hot 100 for 7 weeks-her longest haul ever. It's a sweet, sentimental ballad about a relationship at its end. The song talks about endings, but representing the beginning of an important Madonna transformation from the sex-starved club-going Dita to the proper, mature, even matronly Evita.

9. "Ray of Light," from Ray of Light (1998)

Since 1993, Madonna had refined her image, taken vocal lessons, restored her credibility, given birth to Lourdes, and even won an award for acting (1996 Golden Globe for Evita, take that you nasty movie critics). Her recovery from Erotica complete, Madonna once again turned her focus back to her principal craft, and released her best album since Like a Prayer. Ray of Light saw Madonna (working with William Orbit) effectively meld pop and electronica, drawing on a multitude of dance, trip-hop, personal, and spiritual influences. "Ray of Light" flies by faster than any previous Madonna hit and earned her a Grammy nomination for Record of the Year.

10. "Music," from Music (2000)

Madonna scored another triumph in 2000, with Music. Still electronic, but different from Ray of Light, with a little more sonic edge--mostly the product of French producer Mirwais. "Music" was its best moment, a thumping celebration of club-going, dancing, and enjoying music for music's sake.

Looking to make a mix CD or iTunes playlist sampler of Madonna? Here's what I suggest: Find radio edits of the above 10 singles and add these eight tracks: "Material Girl," "Crazy For You," "Live to Tell," "Justify My Love," "I'll Remember," "You'll See," "Frozen," and "Hung Up." The whole thing should come in just under 80 minutes (the CD maximum).