20+20 = MADONNA'S 40 BEST SONGS

Picture it: Minneapolis, 2020.

Chris Bordeaux has been in self-quarantine for a month due to COVID-19. After a digital happy hour with friends he decides to play some of his favorite Madonna tracks. Then it dawns on him:

I should share my best-of-Madonna list with the world! Her top 40 by 2020!

Obviously.

Madonna's 40 Best Songs

Madonna and Chris Bordeaux - Joke

Jump to today and I’ve realized this is a harder task than I had planned. I couldn’t keep the list to only commercial singles, as this would leave out some of the best songs Madonna has recorded. How could I limit myself to 40 songs when so many hits wouldn’t make the cut?

The following list contains a mix of catchy melodies, touching lyrics, stellar production value, organic artistry, and cultural success.

You may be surprised to learn of the songs, including Holiday, Material Girl, Open Your Heart, and Ray of Light, that didn’t make the cut. Amazing pop hits, but not on my list of Madonna’s top 40.

There will be disagreements. You will be right, I will be wrong.

Just kidding, I’m always right.

Pour yourself a drink, take a journey through our collective memories, and escape solitude with some of the best music from pop music legend, Madonna.

40. Survival

Released: 1994
Album: Bedtime Stories

By the mid-nineties, Madonna was feeling the R&B vibe while collaborating with producers like Dallas Austin. The pair wrote this opening track of her sixth studio album and created a non-radio anthem for Madonna fans who celebrate taking chances to survive.

“Here’s my story: no risk, no glory.”

39. Impressive Instant

Released: 2000
Album: Madonna

Rumor has it Madonna wanted to release this song as a single, but Warner Brothers disagreed. Even without radio play, the song became Madonna’s 27th #1 song on Billboard’s Dance Club Songs chart.

“You’re the one that I’ve been waiting for. I don’t even know your name.”

38. Causing A Commotion

Released: 1987
Album: Soundtrack – Who’s The Girl

This song peaked at #2 on Billboard’s Hot 100 chart in late 1987 – without a music video! It was during eighties Madonna Madness and she produced huge hits solely by performing them on tour. The pushing baseline and punchy chords of this track are *classic* Madonna.

“It’s not a secret how I feel when I stand next to you.”

37. Love Song (featuring Prince)

Released: 1989
Album: Like A Prayer

This song has Prince all over it! His signature sound, for sure. Madonna and Prince co-wrote the track. It appears they shared a mutual respect as successful artists until Prince’s passing in 2016, but I suspect neither one liked working with each other enough to make it happen again.

“Nowhere to run, nowhere to hide. That’s how I feel, don’t fuck my mind.”

36. Heartbeat

Released: 2008
Album: Hard Candy

This album is so tough for me! It… doesn’t fit in Madonna’s catalogue for many reasons. However, I’ve always enjoyed Heartbeat. Madonna singing about dancing? Fuck yes! Her booty getting down during a corny break? Fuck no.

“For me it’s an escape. Does dancing make you feel beautiful?”

35. Till Death Do Us Part

Released: 1989
Album: Like A Prayer

This haunting track was written by Madonna and Patrick Leonard during her divorce from then husband Sean Penn. “We worked in a very isolated place in the Valley,” said Madonna. And it sounds like it. Even people I know who can’t stand Madonna like this song.

“The bruises, they will fade away. You hit so hard with the things you say.”

34. Love Spent

Released: 2012
Album: MDNA

Heartbreak sucks, and knowing someone also used you for your money or status makes it worse. Anyone who has been taken advantage of can feel the pain in this ballad.

“I want you to hold me like you held my money.”

33. Everybody

Released: 1983
Album: Madonna

Madonna’s first single and a time before the polish and budgets. Even before she was a “somebody,” Madonna was crafting catchy hooks. This song makes me wish I was alive and living in New York during the early eighties. I mean, that brown jacket vest?!?

“I’ve been watching you. I see you sitting there by yourself. Yeah. Come on.”

32. Beautiful Stranger

Released: 1999
Album: Soundtrack – Austin Powers: The Spy Who Shagged Me

I remember the summer this song was a jammer: everyone I knew would sing along when it played on the radio. It’s also great to hear Madonna sound like she’s having so much fun in the chorus.

“To know you is to love you.”

31. Where’s The Party

Released: 1986
Album: True Blue

What’s my favorite thing about the queen of pop? Her music offers positive escapism. This song may be the embodiment of such talent. I physically desire throwing a party when I hear this!

“Don’t want to grow old too fast, don’t want to let the system get me down.”

30. This Used To Be My Playground

Released: 1992
Album: Soundtrack – A League Of Their Own

Who doesn’t start singing with the ending credits after A League Of Their Own? No one I know. Another #1 Billboard Hot 100 hit for Madonna.

“The best things in life are always free. Wishing you were here with me.”

29. Angel

Released: 1984
Album: Like A Virgin

This bop skews simple and easy, which is also it’s charm and appeal. A love like this track would really be a wish come true.

“You must be an angel, baby. Clouds must disappear.”

28. Hollywood

Released: 2003
Album: American Life

Madonna’s sarcastic tribute to the reality that is Hollywood. I could never tell if she really disliked the game, given her mastery of playing it.

“How could it hurt you when it looks so good?”

27. Drowned World / Substitute for Love

Released: 1998
Album: Ray Of Light

After Madonna became a mother, her music turned more introspective and spiritual in nature. This song beckons the listener to review their substitutes for love.

“Should I wait for you, my substitute for love?”

26. Bad Girl

Released: 1992
Album: Erotica

A ballad acknowledging one’s bad side. We all have habits we want to change. We do things we shouldn’t. How long can we continue doing them?

“What can I do? I don’t wanna feel blue.”

25. Miles Away

Released: 2008
Album: Hard Candy

Madonna’s ode to long distance love. It’s not all missing-each-other and romanticizing what’s not there.

“Too much of no sound, uncomfortable silence can be so loud.”

24. Gone

Released: 2000
Album: Music

This song has always held a special place in my heart. Leaving before crisis, losing faith, turning to stone. The lyrics aren’t specific enough to alienate, and the melody is beautiful.

“Dream away your life, dream away your dream.”

23. The Power Of Goodbye

Released: 1998
Album: Ray Of Light

The strings and distorted synths of this song combine with Madonna’s vocal to create a fantastic ballad. I mean, that interlude at 2:48? Magic.

“Learn to say goodbye. I yearn to say goodbye.”

22. Intervention

Released: 2003
Album: American Life

The abundant love and care to craft in this masterpiece are self evident. Has Madonna ever felt more… authentic?

“I’ve got to save my baby, because he makes me cry.”

21. Keep It Together

Released: 1989
Album: Like A Prayer

This song has made the greatest impact on me when far away from my family. A connection, written to her brothers and sisters. Is there anything that triggers or comforts more than family?

“Blood is thicker than any other circumstance.”

20. Rain

Released: 1992
Album: Erotica

I remember this striking song from childhood like it was yesterday. As an adult, I admire the rich tones and effortlessness of it all.

“Your love’s coming down like rain.”

19. Lament

Released: 2004
Album: I’m Going To Tell You A Secret

Madonna’s live, and brief, rendition of this song from Andrew Lloyd Webber’s Evita has always registered to me as one of her most striking performances. She really can sing!

“Remember, I was very young then. And the year was forever and a day.”

18. Bitch I’m Madonna

Released: 2015
Album: Rebel Heart

Honestly, I don’t want to like this song on face value. It does borderline on the obscene. But bitch, she’s Madonna. Where’s your boss jam about yourself?

“Bitch, I’m Madonna.”

17. I Deserve It

Released: 2000
Album: Music

Raw and pure while also filtered and structured. Madonna does such an amazing job of combining the juxtaposed. And the lyrical content reminds me that I will be ready for the love I deserve.

“This guy was made for me, and I was made for him.”

16. Into The Groove

Released: 1985
Album: Soundtrack – Desperately Seeking Susan

Quintessential Madonna. Day drinking in the summertime, dancing with friends in the club, driving along the beach with the wind at your fingertips, riding public transit solo. East coast, west coast, and everywhere in between. It all works.

“Touch my body, move in tight. Now I know you’re mine.”

15. Why’s It So Hard?

Released: 1992
Album: Erotica

Madonna was revolutionary in her public support of the LGBTQ+ community. At a time when being in the closet wasn’t only for gay people, Madonna stood proud and shone a spotlight on equality and fair treatment for all.

“Why’s it so hard to love one another?” Why’s it so hard to love?”

14. Ghosttown

Released: 2015
Album: Rebel Heart

With a little foreshadowing-lite for the events of 2020, Madonna knocked it out of the park with this adult contemporary hit. Powerful without being over-powering.

“I know you’re scared tonight. I’ll never leave your side.”

13. Frozen

Released: 1998
Album: Ray of Light

Frozen served as an introduction to a more mature Madonna in the late nineties. Another powerful William Orbit produced interlude from this album at 2:55.

“You’re frozen when your heart’s not open.”

12. In This Life

Released: 1992
Album: Erotica

Madonna has raised millions of dollars for HIV/AIDS research throughout her career. She not only served as a poster child for activism and awareness, she also shared personal stories of love and loss in her life.

“People pass by and I wonder who next? Who determines who loves best?”

11. Like It Or Not

Released: 2005
Album: Confessions On A Dancefloor

An ultimate “Fuck you!” to anyone who tries to put you in a place and keep you there.

“You can love me or leave me, cause I’m never gonna stop.”

10. American Life

Released: 2003
Album: American Life

Originally tossed aside by the mainstream music establishment for some reason, I always enjoyed this song. It was poignant when it was released and is still pertinent now. Even with Madonna rapping.

“I’m just living out the American Dream and I just realized that nothing is what it seems.”

9. 4 Minutes (featuring Justin Timberlake & Timbaland)

Released: 2008
Album: Hard Candy

Okay. This is just good ole’ fashioned pop collaboration fun. I happen to think Timbaland’s production on this song was great, and Madonna and Timberlake have a natural “coolness” together.

“Just say the word and I’mma give you what you want.”

8. Promise To Try

Released: 1989
Album: Like A Prayer

A striking ballad, clearly written and sang from the heart. You can feel the pain and sadness in Madonna’s voice. A beautiful collaboration with Patrick Leonard on arguably her best album.

“I fought to be so strong. I guess you knew I was afraid you’d go away, too.”

7. Live To Tell

Released: 1996
Album: True Blue

Another Patrick Leonard co-produced song, originally featured on Sean Penn’s film At Close Range. For many, this was the first time they heard Madonna sing with such passion. It is still regarded by many as her best ballad.

“The light that you could never see, it shines inside. You can’t take that from me.”

6. Music

Released: 2000
Album: Music

This song has a special place in my heart. I was 16-years-old and Madonna was cool. Like, actually cool. It was amazing. As a homo from a small town in the Midwest who loved Madonna, I can tell you, it meant something. Turn up the volume!

Music makes the people come together, yeah.

5. Like A Prayer

Released: 1989
Album: Like A Prayer

Upon it’s release, this song was surrounded by controversy. And like much of Madonna’s music overshadowed by outrage, what remains is an incredible song, enjoyed by countless people around the world.

“Life is mystery. Everyone must stand alone.”

4. Take A Bow

Released: 1994
Album: Bedtime Stories

Backed by pentatonic strings, this Madonna ballad, produced and written with Kenneth “Babyface” Edmonds, spent seven weeks at #1 on the Billboard Hot 100. I’m surprised by the number of people who say, “Oh! This is Madonna?” when they hear it. A pop masterpiece, in many ways.

“It comes so easy when you get to the part where you’re breaking my heart.”

3. Express Yourself

Released: 1989
Album: Like A Prayer

Empowerment on steroids. Composition crafted in excellence. This masterpiece is for little girls in dance studios, women and gay men everywhere, and anyone else who wants to feel powerful and fabulous.

“Don’t go for second best, baby. Put your love to the test.”

2. Hung Up

Released: 2005
Album: Confessions On A Dancefloor

This banger was everywhere. It was a #1 hit in 41 countries around the world, but not in America. Madonna was too old for radio play in the U.S., even back in 2005. But honestly, if you ever want to strut down the sidewalk like you own the street; put on your headphones, play this song, and just fucking do it.

“You’ll wake up one day, but it’ll be too late.”

1. Vogue

Released: 1990
Album: Soundtrack – I’m Breathless: Music From & Inspired By The Film Dick Tracy

It may be cliche’, but this homage to queer underground ballroom dance combined with Hollywood nostalgia is iconic. I would argue the most recognized song with supporting cultural impact from a female recording artist in modern history. Disagree? Prove it.

“Soul is in the musical, that’s why I feel so beautiful.”

April 9th, 2020|Pop Culture|