The 20 Best Madonna Songs

Nicole Hogsett
The reigning Queens of Pop is arguably the most popular and controversial artist of her time. It's almost as if everything Madonna touches turns to gold - and that has been an amazing gift for her devoted fans, those who have followed her career from the very beginning to young girls just now learning the power of Madonna. That just may be the case with Glee's young fans who will be treated to a Madonna-centric episode Tuesday April 20th. And with such an amazing songbook to choose from, how could the episode fail to excite viewers or live up to the hype? Below are 20 of Madonna's best songs to date...

20. Cherish

The snappy song has a fun beat that makes you want to dance and the rapid-fire lyrics about a girl and boy in love makes the listener want to sing-along. The song is the epitome of a pop song, from the beat to the lyrics, but it works.

19. Justify My Love

The spoken word come-on's that Madonna moans to a lover against a soft beat makes Justify My Love the sexiest song Madonna has ever recorded. The singer has always been sexual, but took it to an extreme with this song and the accompanying video.

18. Don't Tell Me

The closest the Queen of Pop has ever gotten to making country music is with this hit single. The song had a slower beat and was sung at a slower pace than most Madonna songs, and the country element to it made the song fresh and new to her listeners. Always innovating and changing, this song just showed another one of Madonna's many sides.

17. Me Against the Music

With Me Against the Music, Madonna went head to head with the reigning Princess of Pop, Britney Spears. The song, an ode to being on the dance floor and moving to the music, found the two singers singing back and forth to one another, almost like a competition. Watching Madonna keep up on the dance floor with the young singer in the music video just made her look all the more ageless.

16. Borderline

The pretty opening notes are complimented by a beat that plays off of them throughout the song as Madonna innocently sings to a man who is stringing her along. Most aren't used to hearing songs where Madonna is in a vulnerable state over a man, but this song proved that she could play the role of the damsel as well as the heroine.

15. The Power of Goodbye

Showing another side to herself, Madonna went dark when she made The Power of Goodbye, a beautiful kiss-off to a man who hurt her. With lyrics like "Freedom comes when you learn to let go" and "you were my lesson I had to learn" the song becomes relatable to anyone who has ever lost a love that they just can't quite shake, although they know they should.

14. Music

One of Madonna's most upbeat dance anthems, she showed that she had no sign of stopping when she released this song. The beat is amazing, and nothing less than what we had come to expect from Madonna and the lyrics are fun to sing along to whether you're in a club or in your car.

13. Crazy For You

Madonna declaring that she loves someone seems as though it would be no easy feat, but with this song she does just that. The song and its beat bring to mind a hazy, lounge club vibe. The song seems like it could be any other pop-star ode to unrequited love, but Madonna's deep vocal and sexy voice makes it something more adult than it seems on the surface.

12. Into the Groove

One of the most fun songs ever recorded, Into the Groove starts off and doesn't stop for approximately 4 minutes. The song has rapid lyrics and a fun beat that gives the listener no choice but to get up and get into the groove while singing into their pretend microphone.

11. Open Your Heart

From the opening notes you know that this song is going to be enjoyable, yet the beat is deceptive because the song is about a woman who can't get a man to open up to her. Yet putting it against the beat and making the song one suitable for the dance floor masks the sad lyrics - unusual since songs with these types of lyrics tend to be overly dramatic, weepy ballads. But Madonna once again showed that she could do whatever she wishes.

10. True Blue

With a very old-school sound and lyrics, the song was a departure from most other Madonna songs. The sound was completely different than anything she had done before and the song truly focused on her vocals, as she pleaded to the man that she has to come to find as her true love. It also presented a rare, innocent Madonna.

9. Take A Bow

From the beat to the lyrics to its 5 minute length, everything about this gorgeous ballad sounds theatrical, which is quite appropriate given that the song finds Madonna, in one of her best vocals and one of her most touching, vulnerable voices, comparing her relationship to that of a show. When she tells the man at the beginning of the chorus that she has always been in love with him, and then proceeds to tell him that he took her for granted, it makes Madonna more vulnerable and relatable than she had ever been.

8. Ray of Light

A pure dance song, Ray of Light showed a fun, light side to Madonna, one that fans don't always get to see but one that everyone knows is there. Ray of Light is a fast-paced song with an eclectic beat that initially surprised and then won over fans of the singer. The accompanying video that features Madonna in front of a rapid-moving city and other scenes perfectly complements the songs tone.

7. Papa Don't Preach

Madonna made telling parents of an impending, unexpected pregnancy oddly fun on this track. The controversial song found Madonna pleading with her dad that she and her baby daddy were planning on keeping their baby and start a new life together. This song proved that Madonna could tackle a serious topic but still keep her signature sound.

6. Material Girl

Her most fun and frilly song, everything about Material Girl feels pink, from the beat to the lyrics that is all about wants - money, jewelry, cars and all the other objects commonly connected to wealth. Her Marilyn-esque aura that she portrayed in the video also comes through in her vocal with her girly squeals and cute come-ons.

5. Hollywood

Late in her career Madonna made an indictment of Hollywood, and all who flock to the town in an attempt to make it big. The song discusses how intoxicating the town can be and the lengths that people will go to in order to become famous. She talks down about the town, and exclaims that she is tired of the image that the mainstream media tries to portray, all in her sarcastic tone.

4. Like a Virgin

An undeniable Madonna classic, Like a Virgin is a flirtatious innocent-sounding (yet not innocent at all) ode to a lover who makes the singer feel like new. From the classic opening notes to the end the song is an undeniable fun discussion of love. It is also hard to listen to the song without the, now infamous, image of Madonna performing the song at the MTV Video Music Awards in wedding garb.

3. Vogue

The five minute dance floor anthem about the popular underground dance is an instant Madonna classic, and arguably her biggest hit to date. Even if you meet someone who somehow knows very little or nothing about the superstar, they know Vogue. Vogue features some of Madonna's best vocals, an amazing beat and a classic, spoken-word shout-out to all of the talented trailblazers who came before her. You'll definitely want to snap and sing along to the electric song.

2. Like a Prayer

One of her most controversial singles and videos, Madonna got a lot of backlash for this religious song disguised as a dance floor hit. The gospel inspired song was another epic Madonna song, featuring a choir and clearly depicting religious images all set to her trademark dance floor beats - further proving that she could tackle serious or touchy issues and still have fun with it. The video sparked lots of controversy, since it featured images like burning crosses. Like a Prayer infuses dance music and religion, and creates a brilliant song.

1. Express Yourself

"Come on girls/do you believe in love/cause I've got something to say about it", the opening lines to one of Madonna's biggest hits, and one of the best girl-power anthems ever is sung in a domineering way, with the singer demanding the attention of the listener, and then with the brilliant pop song that follows, she doesn't let them go. Madonna has always put out the persona of being a strong, independent female who wouldn't settle for a man she thought was less than worthy, and with this song she encourages all girls to follow suit, in an attempt to get female fans to respect themselves.


Published by Nicole Hogsett

I love to write - not a day goes by that I don't write something. One day I hope to do this professionally, right now I am having a great time writing on Associated Content! Hopefully you enjoy the articles...  View profile


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  • Alyce Rocco4/19/2010

    One and two are probably my favorites ~ Spotight, Holiday, Who's That Girl would bump several of your top picks.