220px-LikeAVirgin1984Madonna – “Into the Groove” – (1985)

Madonna’s second studio album Like a Virgin had its share of hits none more dance-worthy than this track, which wasn’t originally included on the album’s release. It was added for a 1985 re-release after being used in the film Desperately Seeking Susan, in which Madonna stared. It’s a synth-infused 80s dance track and a fine example of early Madonna.

#48 – Madonna – “Music” – (2000)

Well this was about the end of the era where Madonna was making music that I really gave a crap about. It was a #1 hit everywhere – the U.S., the U.K., and all over Europe and Australia. The video, for whatever reason, features Ali G. The song is electropop and was a big hit on the dance chart. Madonna has leaned that way since – toward club music, that is – and hasn’t had near the success – as this crossed over quite successfully onto pop radio where her later hits stayed mostly in the clubs. I want to say “everyone’s career has to flame out sometime” but she is the queen of comebacks. So we’ll see.

#16 – Madonna – “Die Another Day” – (2002)

People really hate this song for whatever reason. Whenever Madonna is involved, things become very polarized. Purists think their “thing” has been invaded by commercialism – because apparently that’s what Madonna stands for (I thought it was phony British accents). This song isn’t that bad, but because it’s Madonna, people love to hate on it. Yeah, the electro-beat is kind of weird – but it was in in 2002. At least it sounds modern, which is a big change from most of the Bond themes.

Madonna – “This Used to be My Playground” – (1992)

I do not like this song. It is sappy and sounds like a lot of the crap that came out in the 80s that was supposed to sound sappy. The lyrical delivery sounds… bored. This was the theme from the movie A League of Their Own – in which Madonna starred. Somehow, it hit #1 in the U.S. for a week – it must have been a lousy week. If you’re into #1 hits like I am, then you’re familiar with it… sorry, I’m falling asleep listening to it as I write this.

Madonna – “American Pie” – (2000)

Madonna didn’t win many friends among classic rock-types when she covered this classic song. And I’m certainly not going to sit here and defend it. She was coming down from the massive high that was Ray of Light and you can definitely hear it in this song. It was released as a single before Music – when her sound kind of changed again. It’s not the full eight plus minute version that Don McLean wrote and recorded in 1971. I don’t think it sounds like she’s going out of her way to butcher it – it’s actually kind of faithful, but with a dance-pop beat. Then again, you just don’t mess with the classics. Plus, she filmed the music video in London. Hey! It isn’t called British Pie. But it might as well have been – it could only muster #29 in the U.S. but it hit #1 in Australia, Canada, Finland, Germany, Italy, Norway, Spain, Sweden, Switzerland, the U.K. and the European Hot 100. So there’s something to be said of its popularity at the time.

Madonna – “You’ll See” – (1995)

While Ray of Light might have been pretty impressive, its predecessor, the compilation album Something to Remember wasn’t exactly trash when it came to 90s-Madonna (this was one of a few new songs on the album). If you listen, you’ll notice a flamenco-sounding guitar and some weird chimes – which basically means it was released in the mid-90s. Madonna had just come off of years (like 10) of being as provocative and controversial as possible and this single was a step out of that light. Yeah, it’s a ballad, but it’s upbeat enough to hold my interest. And the singing is pretty good too.

Madonna – “Dress You Up” – (1984)

Like a Virgin was Madonna’s second album and this was the final single from that album and it marked Madonna’s sixth straight Top 5 single in the U.S. This dance-pop song is classic Madonna – but I’m going to be honest: if this song comes on when I’m out driving with all the windows rolled down, I might leave it on – but I’m definitely turning it down so no one else can hear it.

Madonna – “Holiday” – (1983)

This was the song that launched a career. It was Madonna’s first hit. It’s an up-beat dance track that made use of the electronic musical gadgetry available in the early 1980s – stuff that the developing hip-hop scene was using to launch their genre. Fun fact: Madonna is credited with playing an instrument on this track: the cowbell.

Madonna – “Like a Virgin” – (1984)

This is one of Madonna’s signature songs and it’s sometimes considered the song that cemented her as a pop icon. It was a #1 in the U.S. (and a handful of other countries) – it was the first single off of her second album (which shared the name of the song). How often does the first single of your second album cement you as a legend? Not very. Madonna’s voice on this track is higher than it is on some of her other songs which almost makes her sound kind of Cyndi Lauper-ish. This song was parodied quite wonderfully by Weird Al Yankovic as “Like a Surgeon.”

Madonna – “Borderline” – (1983)

“Borderline” was Madonna’s fifth single and first top ten hit. It was also the last single from her self-titled debut album. Listening to this song again now, the music really sounds dated. It’s very early-80s-ish… which isn’t necessarily a bad thing.

#54 – Madonna – “Like a Prayer” – (1989)

This list almost went without a Madonna song and any 80s music list without a mention of Madonna is surely incomplete. Luckily, Lipps Inc released their album Mouth to Mouth (which contained “Funkytown”) in 1979, thus making it ineligible to be on this list. I almost went with it anyway, but that wouldn’t have been fair to the Sugarhill Gang or Gary Numan, who were also both bounced from the list at the last second. I think this is one of the best songs of Madonna’s career (right there with “Vogue” and “Ray of Light”). The gospel choir (who were probably unaware at the time of recording this song just what exactly the music video would contain – burning crosses) really adds to the song. If anyone actually cares enough to find Lady Gaga shocking, they should take a look back to Madonna (her entire career) as she shocked and angered more people than Lady Gaga can ever dream of.

#39 – Madonna – “Vogue” – (1990)

This album’s full title is I’m Breathless: Music from and Inspired by the film “Dick Tracy.” I forgot Madonna was even in Dick Tracy – her performance was that memorable. This song, however, is quite memorable. The beat is quite dance-y and the best part is where Madonna starts rattling off “vogue” stars from the Golden Age of Hollywood: Greta Garbo, Marilyn Monroe, Marlene Dietrich, Joe DiMaggio, Marlon Brando, James Dean, Grace Kelly, Fred Astaire, Jean Harlow, Gene Kelly, Ginger Rogers, Rita Hayworth, Lauren Bacall, Katharine Hepburn, Lana Turner & Bette Davis. Perhaps the real reason I like this song so much, other than its catchiness, is the fact that I love the Golden Age of Hollywood. Madonna had a hit record in 1995 with Something to Remember and its hit singles “I’ll Remember” and the slightly haunting “You’ll See.”

#79 – Madonna – “Ray Of Light” – (1998)

Ray of Light was Madonna’s best effort from the 90s (or ever). Some of the music on this album, especially this song, was more electronic in style than the straightforward pop style everyone was used to from her. This song borders on trance music and the music video was available in “Special Edition VHS” format (how 90s is that?). Some other singles from this album include “Frozen” and “The Power of Good-Bye” – although in 1999 she had a hit with the theme to the second Austin Powers movie with “Beautiful Stranger.”