From 19 to No. 1: The best of Madonna

I don’t want to make you feel old, but Madonna will turn 60 in 2018. Did that do the trick? Good. Sure made me feel old!

I’m old enough to remember when Madonna first hit the charts in 1982-83 at the ripe old age of 24, ancient compared to some of today’s tween stars. Madonna had been “Burning Up” the dance club charts before breaking through with “Holiday” in 1983. However, I gotta tell you: Nobody thought she was necessarily a huge star after her first two or three chart singles. Her chart resume was good but not great after a year in the spotlight.

And then she set every TV in America on fire on one unforgettable September night.

Billboard magazine tells the story of a few pre-show drinks at the MTV Video Music Awards on Sept. 14, 1984. Madonna stepped down from a giant wedding cake, in a hot white wedding dress, lost a white stiletto and started rolling around on the stage to the delight of every teenage boy in America as she sang her first No. 1 hit, “Like A Virgin.”

Truth be told, watching it back, I’m mostly amazed at how stark the production was compared to today. I’m also remembering her iconic appearance to have been much more risque than it actually was. Compared to some stuff we’ll see on awards shows these days, this was kind of tame.

But believe me when I tell you that Madonna became a star that very night. It changed everything.

Madonna was the decade’s biggest female pop star, and she was its most important. I would argue that Whitney Houston was the decade’s most talented, but I would also argue strongly that Madonna has never gotten enough praise for her musicality. No, the Michigan native was never the best vocalist, but all 19 of her Top 40 hits in the 1980s were musically interesting. They were largely all more sophisticated than the typical three-chord stuff we hear today. Madonna’s songs were equally catchy, interesting and often lyrically provocative, in an era when we shocked rather easily. They are all still listenable.

You can say a lot of things about Madonna Louise Ciccone, but she was never formulaic.

She charted her own path, forged her own style and had an influence on pop culture that I don’t think anybody comes close to matching today. Style and fashion aren’t my areas of expertise, but I can take you on a guided tour of Madonna’s 19 Top 40 hits during the 1980s, ranking them from the least awesome to the most totally tubular.

One note: “Into the Groove” is not on this list because it was never a Top 40 hit. Mind you, this massive radio hit from the movie “Desperately Seeking Susan” was named by Billboard magazine to be the ‘Dance Single of the Decade.’ However, because it was the B side of the Top 40 hit, “Angel,” it was ineligible to chart. For what it’s worth, I would have ranked it No. 4 out of 20. The video was among her best, too.

Let’s count it down.

19. “True Blue” This was the title track to Madonna’s 1986 album, and it got as high as No. 3 on the Top 40. The arrangement was structured like a 1950s tune, and it came during Madonna’s ‘Sean Penn’ short-white-hair era. Good but not great.

18. “Causing a Commotion” This is how good Madonna really was in the 1980s. This was one of a couple hits from her 1987 movie, “Who’s That Girl,” and even children of the 80s barely remember it. However, it hit No. 2 on the singles charts, and it sounds just fine today.

17. “La Isla Bonita” Think about today’s artists and their penchant for playing it safe, and then consider how different most of Madonna’s singles sounded. This was the third single from the album “True Blue,” and it peaked at No. 4 on the American singles charts. It topped the charts in Canada, France, Germany, Switzerland and Great Britain.

16. “Express Yourself” The second single from the album “Like A Prayer” topped out at No. 2 on the singles charts and was probably a bigger radio hit than how I have it ranked here. However, there are a handful of Madonna’s tunes that I think were underrated, even for her catalogue. This one, I think, was perhaps a bit overrated.

15. “Lucky Star” Madonna’s third Top 40 hit was her first Top 5 single, and I think it was her best video — an all-time great in that category just for being iconic. Not that it was the inspiration for Beyonce’s “Single Ladies,” but watch that and then watch Madonna’s video and soak in the understated cool that was early-era Madonna.

14. “Holiday” This was Madonna’s first chart hit after three tries, one of three chart hits from the 1983 album “Madonna.” Musically, it reminds me of ABC’s “The Look of Love,” one of the many great early-1980s songs I’ll expound upon on this blog. However, it got Madge into the chart game, if you will, peaking at No. 16.

13. “Papa Don’t Preach” Between Madonna’s crucifix fashions and references to virgins, there was little doubt that Madonna was Catholic. However, her 1985 No. 1 hit took it to a new level with this moral conundrum of a pop song.

Early in the song, Madonna proclaims to know right from wrong before singing this in the chorus:


Papa don’t preach, I’m in trouble deep

Papa don’t preach, I’ve been losing sleep

But I made up my mind, I’m keeping my baby, oh

I’m gonna keep my baby, mmm…

Madonna is neither musically formulaic nor socially predictable. This wasn’t my favorite song but I’ll be damned if it won’t get stuck in your head without much effort.

12. “Who’s That Girl?” The title track from the movie soundtrack of the same name, “Who’s That Girl?” was a chart-topper in 1987. This was one of Madonna’s most forgettable tracks in terms of pop culture impact, but it’s another of those songs that I would say proves her musical worth. And for the record, she’s dressing as if she had been watching Scritti Politti videos.

11. “Oh Father” I remember writing about George Michael on Facebook, noting that his best song in my opinion was one of his deepest if not his most popular, “Praying for Time.” I’m reminded of that as I place “Oh Father” at No. 11 on this list of Madonna’s best for the decade. What it didn’t achieve in typical Madonna pep it did in gravity, and it was sorely underrated musically. For what it’s worth, this was her worst-charting song of the decade, peaking at No. 20 on the American singles chart.

10. “Like A Prayer” We’re back to the religion on display, and as I recall, this one had the Catholic church all in a tizzy because of burning crosses, dancing in neglige and various Catholic imagery. However, the song was beautifully backed by Andrae Crouch’s gospel choir. The truth is, Madonna was much more thoughtful and respectful than not in most ways regarding her themes. And while there aren’t many Madonna songs that made you sit back and say, “Damn, she’s got some soul,” this track came as close as anything she did, and it was a worldwide No. 1: United States, Australia, Canada, Italy, Spain, Switzerland and Great Britain.

9. “Open Your Heart” The songs from here on out, for me, are all great. Madonna had five singles released from the album, “True Blue,” the most by a lot of any album in the 80s for here. This was the fourth single, and it came with a very enjoyable video where a little kid waits outside while Madonna works the peep show inside. I’m positive I’m not doing it justice, so I’ll leave you to it. And, again, I’ll empathize if the song gets stuck in your brain for hours.

8. “Dress You Up” Madonna wrote many of her own songs, but this was not among them. It was included on the “Like A Virgin” album mostly because she liked the lyrics. It peaked at No. 5, her sixth-consecutive Top 5 hit, but I liked it because musically it carried a melody that could have been part of an older jazz standard. Quick side note: Watch the video and tell me she’s not dabbing at :37 into it.

7. “Angel” Here’s where I’ll get a bit passionate about Madonna. This is a delight to the ears even if it’s a track that doesn’t get mentioned much from her catalogue. The production is smooth, the bass is booming and it’s a great track to dance to in the car when nobody’s looking. It peaked at No. 5 in late 1984, early 1985. To me, this might be her most underrated song. The songs I have at No. 3-1, many 1980s aficionadoes adore. This one, I don’t know.

6. “Material Girl” It’s not so much that I love the song, it’s that this woman is called the “Material Girl,” and the video is as iconic as any that were made in the 1980s. Besides, as I noted earlier in this post, everything Madonna did musically in the 1980s was interesting at worst. Juxtaposed against her previous hit, “Like A Virgin,” this was quite the change of pace.

5. “Live To Tell” When one thinks of Madonna, one doesn’t think “balladeer.” However, two of my favorite Madonna songs, two of them in the Top 5 were ballads. This track was made for Sean Penn’s movie, “At Close Range,” during the time when they were together. It was also included on the album “True Blue,” the first of five singles from that CD. As a musician, I listen to the melody and the progressions and am fascinated by how not formulaic this song is. And if you’re curious: She wrote it. (Note: She co-wrote it. Very few huge pop songs are credited to just one writer.)

4. “Like A Virgin” This was not only Madonna’s first No. 1 hit, it was the song that launched her from fame to uber-fame. Written by Billy Steinberg and Tom Kelly, this smash stayed atop the Billboard singles charts for six weeks. The VMA appearance launched it into the annals of pop culture history, but the song itself held enough greatness to put it at or near the top of all sorts of all-time and end-of-decade charts. In addition to that, I have to give it props for having one of the better opening lines in all of pop music: “I made it through the wilderness. Somehow I made it through.”

3. “Cherish” These last three songs I would include on my personal decade-favorites lists. In fact, for my taste, I would say that Madonna had three truly great songs, this being the first of them. The song is joyous, playful, super positive and catchy as all-get-out without being formulaic, to repeat a theme I’ve focused on throughout the blog. The song was the third single from the “Like A Prayer” album in 1989 and peaked at No. 2. It’s tough to listen to this song and not come away with good energy.

2. “Crazy for You” The first thing I would tell you is that in a decade filled with good soundtracks, the CD from the movie “Vision Quest” was among the best. The second thing I would tell you is that “Crazy for You” might be the best ballad by any singer of the decade. Sure, there are some just as good, but I can’t think of any better. This was Madonna’s second No. 1 hit, and I’ve always loved that two-chord hook that takes you into the verse. It’s something I’ve used from time to time when I write songs.

1. “Borderline” Greatness. This isn’t merely my favorite song from Madonna, it’s one of my 25 favorite songs of the entire decade, regardless of genre or performer. It’s melodically beautiful. The production is smooth. It’s soulful. And it was her second chart hit ever, her first Top 10 track, and it still gets radio play today.

Because it’s terrific.

Take that, 2017. 1983 totally kicks your musical tush.

By the way, I would be remiss if I didn’t acknowledge that “Borderline” was written by a fellow named Reggie Lucas, who was best known for his work with Mtume and for co-writing Stephanie Mills’ hit “Never Knew Love Like This Before.” Go listen to that song, and soak in the similarities between it and “Borderline.”

I’m such a big fan of this song that I sat down and did a cover version of it AFTER I had written this blog post. Love this song. Hope you enjoy the cover!

That’s my list in all its glory. If you enjoyed the post or taking this li’l trip down memory lane, I’d love it if you stopped by periodically. I’ll be posting a few times every week on songs, videos and topics that mean quite a bit to those of us who grew up during the era.

PHOTO courtesy of Nasser Al Nasser. Check out his entire photostream on Flickr!


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