[BRIGHTCOVE “30409275” “” “” “auto” ] The best-named greatest hits compilation ever, Madonna’s The Immaculate Collection, first hit shelves 25 years ago this week – on Nov. 9, 1990.
At the time the album was compiled, Madonna was mining less than a decade’s worth of hits. (The oldest, “Holiday,” debuted on Sept. 7, 1983.) However, The Immaculate Collection is easily one of the best greatest hits albums ever, and over the years it’s risen to become the 26th-best-selling album ever, right behind the soundtrack to Titanic and in front of Metallica’s Black Album.
But what are the best tracks? (And in asking that, what are the best songs of the early phase of Madonna’s career?) We took a stab at ranking all 17 of them, and while we’ll try to talk through how we determined the ranking, do feel free to tell us in the comments how we did your favorite Madonna track a disservice by not giving it the No. 1 spot. (We’re expecting complaints.)
17. "Rescue Me"
It’s not a knock against the track, but when you’re the new single that’s not “Justify My Love” and you’re debuting on a greatest hits album, you’re going to look like the slacker. “Rescue Me” is a solid Madonna track; it’s just not as iconic, celebrated or important as every track on The Immaculate Collection.
Classic early Madonna, classic dance pop. Originally released Feb. 15, 1984, “Borderline” is catchy but in the context of The Immaculate Collection seems more like a promise of even better things to come.
15. "Crazy for You"
A ballad that has easily outlived its origins as the love theme to the 1985 Matthew Modine drama Vision Quest, “Crazy for You” was Madonna’s second No. 1 single on the Billboard Hot 100. So it’s an important part of Madonna history, but perhaps not one of the first tracks anyone thinks of when they recall Immaculate Collection.
14. "La Isla Bonita"
The fifth single off the 1986 True Blue album, the song has gone on to become one of the songs Madonna has frequently incorporated into her live shows, so it seems like one of her favorites. Chart-wise, “La Isla Bonita” hit the No. 1 spot on the Billboard Adult Contemporary and Hot Dance Singles charts and climbed as high as No. 4 on the Top 100.
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It’s Madonna Lite. And that’s not to say it’s not good, but in the context of Madonna’s career, songs like “Cherish” – bouncier, poppier songs in which she’s reigning in the sex appeal – are the outliers. Of that group, “Cherish” is one of the best, but perhaps not as much one of the songs we’d think of as being iconically Madonna.
12. "Open Your Heart"
And now we’re getting into the good stuff. Released Nov. 12, 1986, “Open Your Heart” is a fun pop song about falling in love. It also happens to be Madonna’s fifth No. 1 single. That chorus is unforgettable, but it’s a minor hit compared to the other major hits of Madonna’s early career.
11. "Live to Tell"
Easily one of Madonna’s better ballads,”Live to Tell” was featured in the 1986 film At Close Range, which starred Madonna’s husband at the time, Sean Penn. It hit No. 1 on both the Top 100 and the Adult Contemporary charts and hit No. 3 on the Hot Dance Singles Sales chart – remarkably, since it’s not the danciest song ever. More than anything, the song is famous for debuting Madonna’s first makeover – a more conservative, retro-glam, Marilyn Monroe-esque look.
10. "Lucky Star"
The only track on the entirety of The Immaculate Collection that the Donner wrote solely by herself, “Lucky Star” is the fourth single from the 1983 self-titled album. Fans might be surprised to learn that song wasn’t a No. 1 hit; it only hit No. 4 on the Billboard Top 100. It’s nonetheless become a enduring part of Madonna’s legacy and a song that she continues to sing in live performances even today.
Another weird one for Madonna fans to consider: While “Holiday” has become one of the singer’s most famous songs ever, it wasn’t technically a huge hit, at least going by its chart performance. The third song from her 1983 self-titled debut album, “Holiday” only ever reached No. 16 on the Billboard Top 100 chart. Madonna clearly doesn’t care about the fact that it wasn’t a chart-topper (and likely neither do her fans), for she’s performed it regularly at her all her live shows since.
8. "Express Yourself"
One of Madonna’s most joyful songs, “Express Yourself” also happens feature Madonna exhorting her fans to accept, love and respect themselves. That sentiment underscores a lot of what Madonna has tried to preach during her pop reign. But as wonderful as the song might be, it was never actually a No. 1 hit. Instead, it peaked at No. 2 on the Top 100. Again, the legacy of the song would overshadow its performance on the charts.
7. "Into the Groove"
The big single from Madonna’s 1985 movie Desperately Seeking Susan, “Into the Groove” was never actually released as its own 7-inch single. Instead, it was a B-side on the “Angel” 12-inc single and therefore never charted on the Billboard Top 100. Nonetheless, it’s a perfect ’80s dance pop song and one of Madonna’s best. Billboard would ultimately honor the song as the Dance Single of the Decade.
6. "Papa Don’t Preach"
Arguably the best track from the True Blue album, “Papa Don’t Preach” gets straight to the heart of a lot of what makes Madonna, Madonna: sex, rebellion against the patriarchy, and a whole lot of Catholicism thrown in. It’s a fantastic song, and it will always be one of Madonna’s best. It’s no wonder it not only hit the No. 1 spot, but also spent two weeks there.
5. "Material Girl"
More than 30 years after this song’s release, we’re still calling Madonna “the material girl.” Clearly the song has staying power; just listen to a few lines and see how the song immediately gets stuck in your head. While it never hit No.1 on the Top 100, the song has proven to be a defining song for Madonna, both representing her public persona in the early years and giving her something to contrast herself against as she matured as a performer.
4. "Justify My Love"
Perhaps the most fascinating chapter in the book of Madonnology (so far), “Justify My Love” was not an existing hit when The Immaculate Collection was released. It was a new song recorded specifically to promote the album, and boy did it work. The story behind its ban by MTV and the resulting sales bonanza Madonna found in marketing the video as a “VHS single” is the stuff of pop music legend, but even apart from all that, “Justify My Love” is a sexy, daring track that’s not quite like anything Madonna had released before.
3. "Like a Virgin"
It’s classic Madonna. It has defined who she is ever since its November 1984 release, and when we remember Madonna 100 years from now, we’re still going to identify her as “singer of hits such as ‘Like a Virgin.’ ” It was her first No. 1 hit on the Top 100, and we can’t imagine a better song to cement her status as an icon.
The newest hit to be featured on The Immaculate Collection, “Vogue” has Madonna namechecking the Hollywood stars of yesteryear, from Greta Garbo to Grace Kelly to Ginger Rogers, and as a result it’s hard not to also think of Madonna as inheriting a bit of their twinkly fame magic as a result. “Vogue” was the world’s best selling single in 1990, and its effects on dance music (and Madonna’s status as a pop icon) have been immeasurable.
1. "Like a Prayer"
It’s not only Madonna’s greatest song but also Madonna in a nutshell – Catholic imagery wrapped up in human sexuality with a dash of commercialism (the video began as a Pepsi commercial) and controversy (oh, just about everything about it). But if you can divorce everything you know about the video and just listen to the song? It’s inspiring.