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What's your Top 5 favorite songs of Madonna? Why?

Updated on December 24, 2011

The Different Looks of Madonna

Although I am not a true Madonna fan, I do have to respect her entrepreneurship she is the ultimate promoter of herself and her “talents”. Madonna is a singer, an actress, a writer, a producer and so much more. Born Madonna Louise Ciccone Ritchie on August 16, 1958 in Bay City, Michigan Madonna is the ultimate entertainer and trend setter. Madonna has been around for well over 20 years and is constantly reinventing herself as she goes. She has been an icon to many. Early on she became known for her works that not only explored sexual themes but also religious symbolism as well, which has received criticism from fans, haters and even the Vatican. When Madonna is present people tend to take notice because she is an artist that is continually pushing the envelope.

As a singer she has 11 albums to her name not including albums that she has appeared on or had several songs on such as the soundtrack to Who’s That Girl where she had 4 out of 9 songs on the album.

  • 1983: Madonna
  • 1984: Like a Virgin
  • 1986: True Blue
  • 1989: Like a Prayer
  • 1992: Erotica
  • 1994: Bedtime Stories
  • 1998: Ray of Light
  • 2000: Music
  • 2003: American Life
  • 2005: Confessions on a Dance Floor
  • 2008: Hard Candy

So far in her singing career she has had 8 tours

  • 1985: The Virgin Tour
  • 1987: Who's That Girl World Tour
  • 1990: Blond Ambition World Tour
  • 1993: The Girlie Show World Tour
  • 2001: Drowned World Tour
  • 2004: Re-Invention World Tour
  • 2006: Confessions Tour
  • 2008: Sticky & Sweet Tour

As an actress she has acted in several movies starting with a cameo in Vision Quest (1985) which she sang a song from the soundtrack, Desperately Seeking Susan (1985) where she played Susan a woman wanted by the mob and a housewife who is desperate to be her, Shanghai Surprise (1986) a movie she starred in with her then husband Sean Penn, Who’s That Girl (1987) where she played Nikki Finn an ex con who is trying to prove her innocence, Dick Tracy (1990) where she played Breathless Mahoney and stars with her then lover Warren Beatty, A League of Their Own (1992) where she played a player on the first female professional baseball league, Body of Evidence (1993) a sexual thriller and Evita (1996) where she played the lead role of Eva Peron to name a few.

As an author Madonna has written several books her first was a book titled Sex which was a coffee table picture book with very interesting and sexual pictures and in 2003 Madonna started releasing several children’s books that she had wrote including the series of children’s books called The English Roses and several other children’s books.

Madonna has numerous songs and albums in her 20+ year career so it is difficult to choose just 5 songs. But here are the top 5 that I choose and the reason why I chose them.

CHERISH from the Like A Prayer Album (1989) –

I chose this song because of the lyrics and tune. It’s a very light and cheerful song and I also like the video to this song. Although it is a simple song it really is uplifting and makes me think about the things that I cherish which always puts a huge smile on my face.

CRAZY FOR YOU from the VISION QUEST Soundtrack (1985)

I chose this song because its one of those sappy songs that reminds me of someone that I used to love. Someone that I thought that I was crazy for but really wasn’t. This song has special meaning for me in that aspect. It just brings back really good memories from a time years ago that I do not mind reflecting back on.

HOLIDAY from the MADONNA Album (1983)

I chose this song because this was one of the first songs that I heard from Madonna and then shortly after they created a dance mix that was played in clubs. It was a great dance song really got you up and moving, this song was fun and entertaining and always got me celebrating.

LIVE TO TELL from the TRUE BLUE Album (1986)

I chose this song because it is really a beautiful song. This is probably my number one Madonna song and it is way above these other four songs. I enjoyed everything about this song from the lyrics to the music and the video as well. I thought the look of Madonna in this video was classic.

TAKE A BOW from the BEDTIME STORIES Album (1994)

I chose this song because not only did I enjoy the song but I also really like the video to this song. It was very sultry and sensuous, I enjoyed the ambiance of the video and it really captured the song. This song also reminded me of someone that basically took a bow and so there are special memories attached to this song as well.

It seems that the songs that I chose were mostly slower songs which I happen to think are her better songs. These are only the top 5 and I could probably choose 5 more that I like and there would be faster paced songs included as well. I also chose songs that had special meanings and memories for me which for me really makes the music complete when you can attach a song to the experience.

Madonna has always brought attention to herself in some way from her looks, her personal life to her music and movies; this has helped to sustain her as an artist in every category she has conquered.


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    • Triplet Mom profile imageAUTHOR

      Triplet Mom 

      7 years ago from West Coast

      Hasan- I totally agree its hard to pick 5. Thanks for your list! Great choices!

    • profile image


      7 years ago

      It's hard to choose five songs only! Madonna is the Queen Of Pop.. I would choose all her songs, lol but if you want a top 5 i would choose:

      5-Express Yourself- because it shows how strong and fearless Madonna is

      4-Vogue - It's a timeless song, and I like all the tours versions and performances of this song.

      3-Open Your Heart- because its melody is amazing! Its music video is great though

      2-Hung Up- It's my all-time favorite dance-disco song, Madonna was so fresh and confident in this era.. the whole confessions is great.

      1-Frozen- This song is simply the best song in the history of music, I can feel every word in it..

      Great job!

    • Triplet Mom profile imageAUTHOR

      Triplet Mom 

      7 years ago from West Coast

      ahostagesituation - I love bad girl because I am one!! You have some great ones on your list! Thank you!

    • ahostagesituation profile image


      7 years ago

      You did a great Job!

      Mine in no order: "Cherish"--it still makes me so happy it's like I ate smiles for breakfast! "The Power of Goodbye." "Like a prayer" --for the song and all the bad-A controversy to go with it when that video came out. "Bad Girl"--because of the song, the video, and the fact that few people ever know it when I mention it. It's a got a great message. "This Used to Be My Playground"--because it makes me think of my grandmother.

      Really she can't do much wrong in my book. Great hub for a person whose not even that big of a fan!

    • Triplet Mom profile imageAUTHOR

      Triplet Mom 

      8 years ago from West Coast

      Thanks for your choices

    • profile image


      8 years ago

      Here's my Madonna's top-5 list:

      1. Ray of Light

      2. Frozen

      3. Vogue

      4. Like a Virgin

      5. Justify My Love

      ^ Why? It is most heard of all her songs.

      Check out her latest news @

    • Triplet Mom profile imageAUTHOR

      Triplet Mom 

      9 years ago from West Coast

      Thank you Cris! I have not heard her latest disc, I am a total old school fan although some of her newer stuff is good, just have not been exposed yet. Those are really good choices and nothing wrong with being sentimental that is what music is supposed to do evoke emotion.

    • Cris A profile image

      Cris A 

      9 years ago from Manila, Philippines

      Didn't know you have a hub about Madonna, I'm a fan! I could fill you in on what will happen next as far as her career goes but I'd stick to your hub's topic. My faves are rain - nice video; ray of light - purely kinetic pop like you've never heard before; Like a Prayer - her most soulful yet; Crazy for you - I'm a sentimental schmuck and The Devil Won't Recognize you from her new disc. Great hub!

    • Triplet Mom profile imageAUTHOR

      Triplet Mom 

      9 years ago from West Coast

      Thank you izettl! Those are great choices! She was and still is reinventing herself. I also like other songs like Oh Father and Papa Don't Preach just because of the topic. She was always controversial and still is; from the kiss with Brittany to her relationship with A Rod. It will be interesting to see what happens next.

    • izettl profile image

      Laura Izett 

      9 years ago from The Great Northwest

      "Like a Virgin" because it was the first pop song I heard when I was kid and first album I got. "True Blue" because it's such a cutesy upbeat love song. And "Express Yourself" because it is truly Madonna's girl power shining through. Strong women like her rock!

      I loved all the pics you have of madonna- the many faces and costumes and hair of Madonna and decades of her reinventing herself.

    • Triplet Mom profile imageAUTHOR

      Triplet Mom 

      9 years ago from West Coast

      Gwendymom you are so right! Songs that are special to me have a special memory attached they are able to take me back to a special moment or period of time in my life.

    • gwendymom profile image


      9 years ago from Oklahoma

      Holiday, Crazy for you, and take a bow. I like them because they take me back to my youth, and thats what a good song should do.


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