Michael began piano lessons at age 7 but put that on hold for a number of decades until he could actually learn to play with two hands. He learned to play guitar when his mother shared some of the mimeographed folksongs she had learned and he learned to play largely by playing through the complete Beatles songbook over and over, like a pop Talmud.

In high school, he helped start a cover band along with a friend (future Grammy-award winning recording artist) Marc Cohn. It was the heyday of both FM radio and the singer-songwriter record album.  Silverstone recalls:

"I'm not sure why, but it never occured to us to write songs. Recreating songs as faithfully as we could to what we heard was what we did. Writing songs would have been like making our own clothes. It seemed only sensible to wear sensible manufactured pants and shirts and shoes like everyone else rather than try to fashion them from raw materials and have to live with the awkwardness of that. It made so much more sense to leave the making of original music it to the professionals, so that the feeling of falling so ridiculously short of that kind of cool greatness wasn't going be something we'd have to contend with. It never even occurred to anyone in the band that we might do original songs, or if it did, we never talked about it. I suppose that at that very moment, feelings just like these created the necessity for Punk--just not in us."

Michael began writing songs to fulfill an assignment in place of a final paper for a college Poetry class when he was 19, and that summer wrote essentially an album's worth of songs, and even played in "coffee houses." But at the moment he might have pursued the life of a musician, at the heyday of the singer songwriter and folk rock, it did not occur to him that it was something you could realize any more than miniature golf could lead to the professional golf tour or circling a skating rink occasionally could lead to the Olympics.

He did have that kind of ambition for writing, not for songwriting. On December 9, 1980, Michael left the Midwest behind and moved to New York City, to attend Columbia University on a scholarship. He had chosen New York because he so admired the Catcher in the Rye, which was set there, and it's author J.D. Salinger who had gone to Columbia. The day he arrived in New York City happened to be the day that the world was mourning John Lennon, who had been killed the night before.

"I have to say, even now, that the connection of the Beatles, New York, and admiration of Catcher in the Rye that brought me to New York got profoundly recast the day I arrived in the city. What conclusion to draw from that, I wasn't sure, but as a practical matter it was definitely a message for anyone who identified with Salinger or the Beatles--let alone both. I didn't know what it all meant at the time, but it definitely seemed like I had gotten to the party at the moment it ended, or like waking up from a dream abruptly. I guess in retrospect, it meant that I had to author my own life instead of looking up to heros. It took a long time to realize I was doing that, and only in retrospect do I see that I couldn't just copy a cultural guru, but had to be on a path that was my own and that would not get confirmed in an obvious way."

After college, Michael taught creative writing in the New York City public schools, and a variety of other places including: Sing Sing Correctional Facility; The College of Staten Island; Hunter College; Medgar Evers College; The Home of the Sages Nursing Home; The Robert Fiance School of Business and Academy of Beauty; and Columbia University. He studied poetry with Allen Ginsberg and taught autobiographical storytelling at Columbia with Spalding Gray, it was all about writing and teaching  for him, and eventually, it led to writing books.

Michael moved with his young family New England from New York City, and when his son entered 2nd grade, so did he. Although his first books were published once he became a teacher, music was something he did with his class, or when singing and reading his son to sleep.

And that is the way it was until 2005 when Michael's friend Marc Cohn was the victim of a random miracle. After being shot in the head during an aborted carjacking while touring with his band, Marc found himself walking out of the hospital without major injury, after the bullet lodged in the skin of his right temple and was easily removed without any long-term damage under local anesthetic.

Feeling immense gratitude not only that his friend was alive, but that he could share the appreciation of that with him, Michael wrote Marc an e-mail, which was a personal message written in poetic language, that was meant to be a poem of mutual consolation and inspiration. "Maybe life was curious to see what you would do with the gift of being left alive," was the core of the message. Marc says he received this at a time that he was open to finding meaning in his experience and so receiving this message, and also hearing a report by journalist Rick Bragg about the response of people in New Orleans to Hurricane Katrina served to open up a creative channel in him that led to what became his first album in 9 years, "Join the Parade" (Decca 2007).

Some time later, when the album was about to come out, Marc called Michael and told him that when he thought he was writing a letter, he was actually co-writing lyrics to a song. "Like it or not, you're part of Rock and Roll now, so set up a company because you are going to get royalties from this." In addition to Marc's vocal, the recording of the song,  Live Out the String, features Jim Keltner (who recorded with John Lennon), Charlie Sexton (who recorded with Bob Dylan), Benmont Tench (keyboardist with Tom Petty and the Heartbreakers), and Amy Helm (vocalist, and daughter of Levon Helm).  

Just when a meteorite
has fallen on the chair you just got out of to answer the phone
will you live every moment like it just might be the last
or will you still just bitch and moan?

Fate is kind
fate is cruel
and its terminally cool
its a random interruption in the the middle of your groove

But sometimes
you gotta get down on you knees
and thank the whole Universe of Gods
for letting you

Live out the string
a little longer now,
raise your voice, 
and make a joyful noise,
ain't no guarantee,
of anything,
so live out the string

           lyrics from Live Out the String (Marc Cohn/Michael Silverstone)
           From "Join the Parade" (Decca 2007)

Astonishingly, to Michael, Marc performed this song on NBC’s “Today Show” and the “Ellen DeGeneres Show”. It was also played at 100 concerts all over the U.S. and beyond. "To me, this was a kind of anti-trauma, an unlikely and unforeseen event that leaves life unexpectedly more wonderful in its wake. Traumas are accepted as common, why not anti-traumas?" Michael asked.

And as one of the side effects of this anti-trauma, Michael started to write his own songs, and he began to do so prolifically, as if catching up to 30 years of songs he would have otherwise written, waking up from sleep with melodies or words, and notating them, compiling back catalog of hundreds of songs while adding new and even better ones, all the time. To play all these songs, he learned to play piano, taught by what he heard in his head, record multi-track arrangements, assemble a band, and enjoy performing. It seldom seemed like work. It all had the ease of something that was harder not to do than to do

"There's this thing that happens when I'm composing and writing, where I feel like something is coming out of nothing and becoming something bigger than I even knew that there could be. To be in that feeling is magical, so I'm just going to stay right on it and let it be all it can as I focus thought and imagination in that place, and see how amazing it can become. When you find a calling, that's what the deal, I understand. I'm not trying to do that as an ambition, I'm listening to the impulse to make music and it's almost involuntary like a kundalini 220 volt current. And because it feels like it has a life of it's own which runs through me I am curious where that will go and where it wants to go. It already feels like it is somewhere interesting."