It’s been a while since I’ve posted a Great Debate with my high school friend Chance.  The last one we did was in 2009.  Of course, he’s been a little busy the last four years.  He graduated from law school, married one of the coolest girls I know and had a kid.  I managed to work in an extra three shows into my already-full DVR before falling in love with salted caramel cupcakes.  Score.

Last time we debated Prince.  You can read about it by CLICKING HERE.  Before that, we went round and round with Michael Jackson.  You can read about that by CLICKING HERE and then CLICKING AGAIN on my first website retraction ever.

I was inspired by Madonna as our next Great Debate topic after attending her concert a few weeks ago.  Well, inspired is probably too bold.  I was actually disappointed by how many popular songs were left off of the set list.  I was equally concerned for my ears and eyes regarding all of the stuff I would never be able to unhear or unsee.  To quote my friend Kristie, “All I could think to do was to pray for her as she tortured those dancers on the stage.”

Amen Kristie.

I haven’t really been on the Madonna bandwagon since her Immaculate Collection CD in 1990.  Since Madonna is all about reinventing herself and all I care about is 80s Madonna, is that just personal preference?  Or am I getting old?

I called Chance to confirm one or the other.

We never connected.  There was a lot of phone tag and quick messages, but nothing was set in stone.  Between watching Vampire Diaries my hectic work schedule and Chance’s baby whisperer ways of training his son to sleep through the night at six weeks, the Great Debate went down via text.

Me:  I need your top five Madonna Songs.
Chance: Live to Tell, Crazy For You, Like A Prayer, Open Your Heart, Papa Don’t Preach or I’ll Remember. I can’t decide.

Me: Live to Tell, Crazy For You and Like a Prayer are on mine too!
Chance: I think I should pick something from the 90s. I hate to think she was at her best 22+ years ago. Damn we’re old. I like that movie with Joe Pesci as the homeless Harvard man.

Me: Vogue is 90s.
Chance: Vogue is not in my top 20.  Papa video was awesome. And the song was a puzzler. What was Papa preaching? Adoption? Because she definitely declared that she was keeping her baby.

Me: With Honors is that movie. What does that have to do with Madonna?
Chance: The theme song was I’ll Remember.

Me: Papa had that hot guy in it.
Chance: Huh?

Me: The video. Hot guy.
Exhibit A:

 

The text messages end there.

I do remember a conversation about how awesome I think “Express Yourself” is and Chance’s uncomfortable shifting on the phone with blatant disagreement. I’m quite confident that he would be on board with this choice in his top five if she started out the song with, “COME ON BOYS? DO YOU BELIEVE IN LOVE? WELL I GOT SOMETHING TO SAY ABOUT IT. AND IT GOES SOMETHING LIKE THIS.”

It’s just a guess. But I have known him for roughly 25 years. That uncomfortable shift spoke VOLUMES.

I can also confirm that the various unofficial polls I conducted with several male friends, “Crazy For You” was always listed first or second among the list. I asked Chance what the deal was with dudes and the Material One’s sultry ballad. His simple response was that he prefers Madonna’s voice in her lower octaves.

Which brings me to “Take a Bow.” It’s the only song I liked on her Bedtime Stories album. It pains me to say that it didn’t make the top five, but I can reveal without a shadow of a doubt that the list below is solid greatness:

– Live To Tell
– Crazy For You
– Like A Prayer (give me a Gospel choir any day)
– Express Yourself
– Holiday

What do y’all think? Did I get it right? Is there something that I completely forgot? Are you like my friend Ann who listed “Lucky Star” in her top five? What about “La Isla Bonita” and how when you sing it, you feel tropical and/or fluent in Spanish? Did you go to the Madonna concert? Were you scared like me? Did you fall asleep before she took the stage? Sound off in the comments section!