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We recently caught up with Monte Pittman to talk about his first solo album for Metal Blade (and his third overall), The Power of Three. And while he’s certainly a renowned enough artist in his own right, he’s also been Madonna’s guitar player for the last 13 years and logged time with Prong, among other endeavors. We asked him to rank his five favorite songs to play from both Prong and Madonna. Here’s what he told us

5) “Secret”
This a great song to play on the acoustic. There are some great chord changes and something to always keep your fingers occupied. On “The Drowned World Tour” in 2001 we did this song. I tuned my guitar down and Madonna played using a capo on her guitar. That was inspired by Joni Mitchell at the time. This way we were both playing the same chords but in two different places on the guitar neck, or inversions, to work together as one part.

4) “Burning Up”
Usually we will take one of Madonna’s songs and make a “rock” version of it somewhere in the set. It’s incredible how so many of her songs can be played in different styles. On the “Reinvention Tour” in 2004, we played this one that way. People sometimes ask me “do you ever do any guitar solos with her?” and I don’t believe in adding a guitar solo just for the sake of showing off. This is a song where a guitar solo made sense and was a lot of fun to play.

3) “Hung Up/A New Level”
I’ll never forget the night I heard the demo for “Hung Up” for the first time. I had just finished giving her a guitar lesson and she had just gotten a CD from Stuart Price of some songs he had been working on to start the “Confessions Of A Dance Floor” album. She put in the CD, and as soon as that song kicked in, you couldn’t sit down! On the “Sticky And Sweet Tour” we ended this song by going into the Main/chorus riff to Pantera’s “A New Level.” The set and one of the themes to the “Sticky And Sweet Tour” built like it was a game. Playing “A New Level” had several meanings to it. It was almost at the finale of the game, paying tribute to Dime, enjoying such an amazing piece of music, and possibly turning new people on to something they might not normally know. Also, when else would you get to jam on some Pantera in front of a sold out stadium of 80,000 people?

2) ”Don’t Tell Me”
This is the song that started it all for me with Madonna. Our first performance together was when she asked me to play on David Letterman with her and this is the song we did. My experience playing in a band like Prong helped me execute the main guitar part live and approach it like I’m playing the individual samples that make up this riff.

1) “Papa Don’t Preach”
This song is pure genius and one of the best constructed pop songs of all time if not THE most. Every part of this song can stand on it’s own. In the multi tracks to this, there are 3 different guitar parts which I assume are 3 different guitar players having their take on the song. It all works together beautifully. I can’t think of another song that has so many parts that could arguably be the part you remember most.

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