Following my post on Madonna’s upcoming career-spanning hits compilation, someone asked me what my ideal tracklisting would encompass.
Like I said, limiting the collection to one disc would not do Madonna or her musical output much justice. With so many terrific and template-making hits, how could a listing of, say, 21 songs represent such a rich history without that history feeling somewhat incomplete? As it stands, 1990’s The Immaculate Collection is a near-perfect compilation of era-defining tracks- but, that leaves out 16 years of hits from the 1992-2008 period, so as strong a tracklisting Immaculate boasts, it doesn’t tell the whole musical story.
With as many hits as Madonna’s had since 1983, she could easily fill two discs, and comfortably spill over to a third. But, not all of the hits would be *essential*- think No. 1 hits like “Who’s That Girl” and “This Used to Be My Playground.” Neither of those get much in the way of recurrent airplay on U.S. radio stations, and neither are that regarded as one of her most beloved tracks. Same goes for some of the dozens of hits she’s scored through the years.
With that in mind, I shall attempt to compile my ideal, one-disc, career-spanning Madonna album. It’s possible that one or two previously unreleased tracks could make the cut, but I’m sticking strictly with the oldie-but-goodies. These 21 tracks encompass the cultural and musical hurricane that has been and is Madonna- huge, fondly remembered hits, that continue to be staples on U.S. radio, and/or engrained themselves into the cultural consciousness via audio, visual or persona-defining means.
I’m aware that a single CD holds a maximun 80 minutes of music, so I leave the editing challenge to Warner Bros.
(And, yes, in case you were wondering, it pains to leave off any of the 15 Immaculate Collection classics. But for this purpose, “Lucky Star” and “Cherish”- as fine and enduring as they are- bit the dust).
1. Holiday: Not even close to being one of Madonna’s biggest chart hits (topping off at No. 16 on the Billboard Hot 100), this track stands as one of her signature tunes and has endured as a timeless anthem. Fun, frothy, celebratory- at its heart, it’s lose-yourself bliss. But even among the light-heartedness, there’s a message: Coming together, unity, peace and harmony. That puts it a few steps ahead of an earlier, similarly themed track like Kool & the Gang’s “Celebration.” Furthermore, it remains the most-performed track of her career- no wonder she gave it a vacation from her last two tours. No doubt it will be back on the setlist in the future (and as more than a request singalong like it was on a couple of 2008 Sticky & Sweet Tour stops).
2. Borderline: Boy-girl romance- it’s a classic theme in the pop arena, and Madonna’s take on it was played out in this tune and video, her first American top 10 hit. Here, she’s a gal who longs to be happy with her lover, but gets wise to his mistreatment. Even from the start, she was no one’s “boy toy.” The video also offered a contrast in lifestyle and male figures- the barrio and the machismo Hispanic boyfriend vs. the glamorous life and pure-bred white male who seemingly could make her a star and give her everything. Whether the song is about an orgasm, as once suggested, is left to interpretation. Often regarded as one of the best tunes and clips of the 80s, the song, like most of Madonna’s 80s hits, is synonymous with its decade, and remains one of her most-heard classics on U.S. radio.
3. Like a Virgin: This signature track- the first of 12 Hot 100 No. 1 hits- had huge impact even before its release, thanks to Madonna’s 1984 MTV Video Music Awards performance, when she writhed around on stage in a wedding dress. Bringing the virgin-whore dichotomy to new and dizzying heights- contradicting the image of the blushing virgin bride with that of a slutty, salacious, wanton female- this track sealed Madonna’s cultural dominance. The fact that the title had the word “virgin” certainly didn’t hurt, either- nor did the ambiguity of the lyrics, which was debated famously in the film Reservoir Dogs. The 1990 Blond Ambition Tour performance- where she’s flanked by two cone-wearing male dancers and simulates masturbation/sex on a bed- brought the track further notoriety (and a near-arrest in Toronto, as chronicled during the documentary Truth or Dare). Wanna-bes Christina Aguilera and Britney Spears- as brides- performed the song at the 2003 VMAs, before Madonna herself- as the groom- popped up and snogged them both. We wouldn’t have had it any other way.
4. Material Girl: As if having one signature track in one year isn’t enough, Madonna landed another in 1985 (with more to come). Who would have guessed that a video clip paying homage to a classic Hollywood film and star would usurp the original? Madonna pretty much did it here, with her materialism-glorified tribute to idol Marilyn Monroe and her film, Diamonds Are a Girl’s Best Friend. Feminists thought she single-handedly set the women’s movement back years by singing about dollars-clad men making the world go round (of course, the irony could be seen in the video, but- as the case often is with Madonna- some failed to see it). The tune itself- tongue-in-cheekily reflected the times during which it was released, perfectly representing the greedy, me-me-me Reagan-era America and Reaganomics. As with “Like a Virgin,” “Material Girl” has endured as a cultural definer, either because Madonna is still referred to as the “Material Girl,” or simply because it summed up its era with style. Also like “Virgin,” “Material Girl” was featured (less prominently) in the 2001 movie musical Moulin Rouge.
5. Crazy For You: From the long-forgotten high-school wrestling movie Vision Quest, Madonna’s first love ballad ranks as one of the rock era’s greatest love songs. No major cultural repercussions here, just heartfelt declarations, set against an intimate musical setting. The song went onto launch a million school dances, undoubtedly, with people swooning at the one who makes his/her heart skip a few extra beats a minute. Madonna gave the No. 1 classic new meaning during her 2004 Re-Invention Tour, dedicating the song to the fans who have stuck by her for the last 20 f***ing years. Crazy for you, indeed.
6. Into the Groove: One of the all-time greatest dance anthems, Madonna-Mania reached new heights with the release of this track, featured in the film Desperately Seeking Susan. Oddly, only commercially available in the USA as the B-side on the 12-inch “Angel” single, “Groove” had little trouble becoming another top 10 airplay smash and a No. 1 seller, shifting more than 500,000 copies in the process. An earlier track, “Everybody,” called for people to get up and do their thing; “Into the Groove” took things further, going as far as to say that “music can be such a revelation… only when I’m dancing can I feel this free.” Madonna gives dancing a high level of importance, perhaps likening it to a religion- an outlet/activity where people could lose their inhibitions and be themselves, a theme Madonna would revisit in yet another later classic. (Also at work in this track is sexual innuendo- the lyrics easily could be referring to sex as much as dancing.) The video, which featured images from Susan, showcased the ultimate “Madonna-Wanna-Be” look that domainated 1985.
7. Live to Tell: An important release for Madonna, in that it was a sorta left-field direction to go, following her last release, “Dress You Up” (which, while left off The Immaculate Collection, wasn’t free from cultural activity, thanks to Tipper Gore and the Parents Music Resource Center citing it among the “Filthy 15.”) Here, the mood was somber, the emotions high (she even dons a conservative school-teacher-like flower dress in the video). Used as the theme from then-husband Sean Penn’s film At Close Range, “Live to Tell” addressed abuse and the heavy-weighing impact it harbors on one’s mind. While not as obvious in its subject matter as Suzanne Vega’s “Luka” (which would come a couple years later), the impact is no less striking. This ballad would raise the bar for Madonna releases thereafter. Twenty years after its initial release,”Live to Tell” was part of yet another worldwide Madonna controversy- performed on 2006’s Confessions Tour, Madonna sang the song while strapped to a mock cruficix. Naturally, religious leaders were up in arms, but Madonna insisted she was illustrating the suffering of AIDS-stricken orphans in Africa. Finally, the song received significant cultural importance to match its popularity.
8. Papa Don’t Preach: Madonna found herself being both criticized and applauded for this tale of a teenager who chooses to keep her unborn child. The track brought the sensitive issue of teen pregnancy to the forefront. Tipper Gore- who included Madonna in the “Filthy 15″ a year earlier for “Dress You Up”- now had nothing but praise for Madonna, saying that any song encouraging family discussion about such a matter is a positive thing. On the flip side, some blasted Madonna for- what they saw as- giving teens the thumbs-up to go out and get pregnant, suggesting she was leading teens on a “path to poverty.” With the No. 1 “Papa,” Madonna again was at the center of a cultural firestorm- where she would land several more times through the early 1990s.
9. Open Your Heart: While this No. 1 single wasn’t controversial in audio form (well, maybe if one looks at”lock”/”key” as innuendo) , the accompanying video was another matter. Madonna plays a peep-show dancer who ends up running off with an under-age boy. He worships the bustier-clad siren, mimicking her dance moves outside the show (for which he is too young to gain entrance)- perhaps a nod to the young boys who did so in their bedrooms (I’m sure gal wanna-be’s weren’t the only ones doing so). Pornography, art, the ambiguous relationship between an adult woman and a little boy (preceding such real-life speculations regarding fellow icon Michael Jackson)- all catalysts for another Madonna flap.
10. La Isla Bonita: Always one to dip into the underground or other cultures to raise others’ awareness (and some say further herself in the process), this track and video clip paid homage to Latin beauty. Long before the so-called “Latin Explosion” at the end of the 1990s, this track was a worldwide smash. And, it wouldn’t be the last time that Madonna gave a nod or two to the Hispanic community in her work. 
11. Like a Prayer: If anyone thought “Like a Virgin,” “Papa Don’t Preach” or any other Madonna controversy up to 1989 was outrageous, they undoubtedly were left speechless with the release of “Like a Prayer.” The No. 1 song, in Madonna’s words, detailed a girl’s relationship with God, but also touched upon the dynamic relationship between religious and sexual ecstasy (as described by video director Mary Lambert). The lyrics left one wondering if it Madonna was looking at the sacred or the profane- or both. The video was even more shocking- images of interracial romance with a black Jesus-like figure, racism, injustice, stigmata, inappropriate church attire; the burning-crosses-infused clip led Pepsi-Cola to cancel Madonna’s endorsement spots (though she reportedly kept the $5 mllion). The Catholic Church condemned her, and the world’s inhabitants were left with yet more taboo material to dwell over at the dinner table, courtesy of pop culture’s prominent provocateur. 
12. Express Yourself: Following the “Like a Prayer” uproar, Madonna upped the ante with this anthemic feminist call, a quasi-update of Aretha Franklin’s “Respect.” The track pushed the “say-what-you-want-or-you’ll-never-get-it” mentality, while the video supplied more material to send feminists up in arms: androgyny, crotch-grabbing, female-pussycat symbolism/metaphors, bondage (Madonna chained to a bed) and a steamy sexual encounter with a guy who won the right to come service her. All the necessary ingredients for a Madonna classic, as well as a water-cooler videoclip. 
13. Vogue: Madonna kicked off the new decade with this dance anthem, updating the themes earlier heard in tracks like “Everybody” and “Into the Groove.” Here, the dance floor is an outlet for self-expression, a place that can make one feel like a superstar- regardless of gender, ethnicity, class, etc. Madonna rustled through the gay/underground closets and brought a then-passe trend to the mainstream- vogueing (dancing while striking model-like poses). Suddenly, the world was striking a pose along with Madonna- a trend further aided by the classic black-and-white video clip, in conjunction with the ground-breaking Blond Ambition Tour and her presentation at the 7th Annual VMAs, where she- in Marie Antoniette garb- danced and frolicked racily with her entourage of dancers. Madonna perhaps was at her most glamorous, and it was this video that not only showcased one of those dandy bullet bras, but also her plentiful assets. While a bit of nipple appeared hastily in the earlier “Papa Don’t Preach” clip, Madonna left absolutely nothing to the imagination here, wearing a sheer blouse that reportedly even made Cher blush. MTV had earlier said it wouldn’t play her “Oh Father” video because of sewn lips, but caved in. The video channel also threatened similar action here, but, once again, bowed to its biggest and brightest star. The song and video- which remains an influential template of style.- also helped cement Madonna as the ultimate gay icon- not that she wasn’t before “Vogue” (after all- she got her start in the underground-club scene, been a dedicated supporter of AIDS research and teased the public with Sandra Bernhardt), but from this clip onward, there was no denying the gay community’s tie to La Ciccone.
14. Justify My Love: One of the then-new tracks on The Immaculate Collection, “Justify My Love” was little more than a spoken aural sex track. However, the video surpassed all past endeavors as her raciest yet. MTV deemed the clip- which featured images of bisexuality, bondage, androgyny, among other alternative activities- as being way too hot to handle, resulting in its banning. Anyone who still had reservations about Madonna’s cultural status look no further- as Operation Desert Storm began to take shape, Madonna- a musical artist/entertainer- was the featured guest on ABC’s Nightline. The video, released at the height of the censorship debate in America, ran in its entirety on the program, while Madonna defended her right to freedom of expression. Shortly thereafter, the video went on sale to the public, shipping more than 400,000 units in America. If the video itself wasn’t enough to cause a ruckus, the track’s co-writer and producer Lenny Kravitz was accused of lifting the rhythm track from a Public Enemy track. Almost simultaneously, Kravitz was called on by former lover Ingrid Chavez, who claimed the song was lifted from a love letter she wrote to Kravitz. Furthermore (!), “The Beast Within” remix featured on the maxi single raised the ire of Jewish leaders, who get angered by a passage from the New Testament, Revelations 2:9 featured in the mix. What caused the flap? “I know your tribulations and your poverty, and the slander of those who say they are Jews. They are not. They are a synagogue of Satan.” Rabbi Abraham Cooper, associate dean of the Los Angeles-based Wiesenthal Center, commented that “the impact of having America’s leading cultural icon say those lyrics can give a powerful tool to bigots.” Madonna insisted she was no racist, and that including the passage on her record was a commentary on evil in general. Nonetheless, the No. 1 “Justify” hinted at Madonna’s Sex-capades to come, in the form of the Sex book and Erotica album.
15. Take a Bow: Madge had put her clothes back on (well, almost all) with 1994’s Bedtime Stories album. Never mind that PETA (People For the Ethical Treatment of Animals) thought she glorified bullfighting with this maiden-bullfighter tragic love-story epic (again calling her out with its sequel “You’ll See”); the video for Madonna’s longest-running U.S. #1 (at seven weeks) featured Madonna simulating self-sex while watching the object of her desire on a large television screen. Probably one thing that led to its huge popularity on video channels. And, the classy, old-school style Madge donned in the clip previewed her turn as Eva Peron in the big-screen adpatation of Evita, for which she- believe it or not- won a Golden Globe as Best Actress. Argentina probably wasn’t crying for her at that moment in time. 
16. Ray of Light: Following two tepidly received albums, Madonna arguably was the first to weave techno and pop successfully with Ray of Light. Like the album, the title track- another top five chart hit- went on to mass acclaim. In the track, Madge sings, “Quicker than a ray of light, I’m flying,” and for the video clip- which also earned mass accolades- she darn well means it, the day-in-a-life clip running at such rampant pace that sales in Dramamine rose following the clip’s release. And, just when her controversy-making ways looked like they were over, she managed to rattle once again. The World Vaishnava Association claimed that she offended both Hindus and Yogis by not only wearing a chastity-, harmony- and purity-symbolizing Hindi mark on her head, but also by wearing the mark while simultaneously simulating a sex act and wearing a see-through tank top. More shocking, though, was learning there was an existing organization that hadn’t previously been offended by Madonna.
17. Music: Pushing the video envelope again, Madonna spoofed hip-hoppers (such as Puff Daddy, who she singled out via a license plate labeled “Muff Daddy”) and cavorted with female strippers, both in a strip club and inside a limo. The No. 1 song- a throwback to the early days and becoming yet another dance anthem- informed how “music makes the people come together”- race, sex, orientation, be damned. In addition, Madonna made the cowgirl look trendy again, thanks to her album art and video style, in both this clip and the Western ho-down look adapted for her “Don’t Tell Me” video.
18. Don’t Tell Me: Incidentally, both “Don’t Tell Me” and “Music” videos were spoofed on MTV’s Movie and VH-1’s Fashion award shows, respectively. Following “Music’s” success, this stop-start track gave Madonna another U.S. top five hit, and has held on reasonably well as a recurrent airplay hit.
19. Die Another Day: The theme to the 20th installment in the James Bond franchise- which itself could double as Madonna’s career motto- did not come without a little controversy. Firstly, Madonna kinda went left-field in what’s considered a traditional Bond theme; sure, it had the dramatic strings and intensity, but it also called on “Music” collaborator Mirawis, who gave it the techno twist and vocal effects. The track- which received some accolades- also received some very public criticism, from the likes of Elton John (calling it the worst Bond theme ever) and one-time Bond warbler Shirley Bassey. The video (which included no film clips, but some re-enactments of key scenes) raised the ire of some in the Jewish community, with its Hebrew tattoos and tefillin (small leather cubes, containing biblical verses and worn during worship). When Madonna is electrocuted by Nazi-like goons, three Hebrew letters appear on the electric chair- lamed, aleph and vav- part of the “72 names pf God” taught in the kabbalah, mystical Jewish teachings studied by Madonna and some other celebs. While the “uproar” wasn’t along the lines of a “Like a Prayer,” some felt that using Jewish religious articles for such non-religious purposes could offend people; apparently, some Orthodox Jews also found it nontraditional for women to use tefflin. Nevertheless, the 20th Bond film becomes a worldwide smash, with the title track bringing Bond back to the U.S. top 10 for the first time since the 1980s.
20. Hung Up: Following the disappointing American Life era (which included Madonna uncharacteristically pulling an anti-war video in fears of offending anyone sensitive to the Iraq War), Madonna returned to the carefree clubs on 2005’s Confessions on a Dance Floor. With “Hung Up,” she sampled Abba and in the accompanying video, donned a leotard and paid homage to Saturday Night Fever and Flashdance. While scoring her 36th top 10 on the Hot 100, Madonna enjoyed one of her bggest worldwide hits to date, proving that the world still was plenty “Hung Up” on the Queen of Pop. 
21. 4 Minutes: Usually one to collaborate with lesser-known producers, Madonna took the least riskiest route fathomable on her 2008 album, Hard Candy, by working with Timbaland, Justin Timberlake and Pharrell. On the album’s apocalyptic-foreshadowing, yet-having-a-good-time-regardless lead single, Madge traded lines with Timberlake, and, in the process, landed her first U.S. top five single in seven years. Some joked that the video’s greatest special effects came in making almost 50-year-old Madge look not so far off Timberlake’s age range. Time, apparently, is waiting for ever-youthful-looking Madonna to age in more rapid fashion.
And, those are the tracks I would compile onto a single-disc, career-spanning Madonna compilation. If two discs, what other tracks would I add to the mix? Obviously the two aforementioned Immaculate Collection classics- but what else? Stay tuned for a possible follow-up…(Images are courtesy of www.madonnalicious.com- thanks, Clare)