Here's the interesting  story about how guitarist Monte Pittman met Madonna, taught her to play guitar  and went on tour with her:
 
 In 1999, Monte Pittman bid a  fond farewell to his rural hometown of Longview, Texas, and headed west to Los  Angeles in search of the big time. But like so many other musicians who have  done the same, Monte found himself in other situations.
 'I got a job  working at a music store selling guitars and sweeping floors," he tells us.  But as fate would have it, that dues-paying gig opened a door that would  change Monte's life. "People would come into the store looking for guitar  teachers," he explains, 'so the thought occurred to me, I could just teach. I  could be my own boss. And that's exactly what he did. "I quit cold, put out  my card, and started looking for students."
 One day a man called the  music store inquiring about guitar lessons, and Monte's name was passed along.  That customer was none other than Guy Ritchie, film director extraordinaire  and soon-to-be husband of Madonna. "Guy was my third student," Monte recalls.  "That was before Snatch came out, and I didn't know who he was. It turns out  he and Madonna were dating. He had just had some surgery done on his knee, I  believe, so he was off his feet and she got him a guitar. He started taking  lessons, and he got pretty good at it."
 'I remember the day Music  (Madonna's CD) came out, and I taught him a few things from it. I thought it  would be cool for him to play them for her."
 When Guy returned the  favor and bought Madonna a guitar, she started taking lessons from Monte as  well. "It was the same thing as Guy - she learned everything I gave her," says  Monte. 'she took it seriously, and worked really hard at it. She learned so  much so quickly. That's one thing about Madonna - her drive is incredible."  
 A month after Madonna started playing guitar, she got called to  perform on David Letterman. 'she invited me to come play with her, and I  thought she was pulling my leg at first," Monte laughs, "but she was serious.'  That gig went well, and it led to a slot on Madonna's Drowned World tour,  which carried Monte through to the current Reinvention tour.