Begin Reading
Table of Contents
Newsletters
Copyright Page
In accordance with the U.S. Copyright Act of 1976, the scanning, uploading, and electronic sharing of any part of this book without the permission of the publisher constitute unlawful piracy and theft of the author’s intellectual property. If you would like to use material from the book (other than for review purposes), prior written permission must be obtained by contacting the publisher at [email protected]. Thank you for your support of the author’s rights.
This book is dedicated to my mother and father; my beautiful daughters, Isa, Holly, and Taryn; and my gorgeous granddaughters, Amelia and Olivia “Gwenny,” who have directed my course and continue to bring me back to the soul of it all.
Introduction
Know then thyself, presume not God to scan;
The proper study of mankind is man.
—Alexander Pope
Hello, I’m Captain Jack Sparrow. At least that’s how I am known to those who’ve racked up more than ninety million views of my viral music video with the Lonely Island guys from Saturday Night Live.
For reasons I’ll explain later, Andrew “Andy” Samberg, Akiva “Kiv” Schaffer, and Jorma “Jorm” Taccone now call me Lord Boltron, while the people from my home state of Connecticut know me by my family name, Bolton.
If you are a radio listener, you know my voice from Top 40, rock, adult contemporary, and R & B stations over the last four decades.
If you were around the Yale or Berkeley campuses or Greenwich Village in the 1960s, you may have known me as the hippie kid who played guitar and sang on street corners for meal money.
Anyone who regularly traveled U.S. Route 66 during that same decade may have seen me along the roadside, either hitchhiking cross-country with my buddies and bandmates or trying to push-start a vehicle that looked like a cross between a Wonder Bread truck and the Beatles’ Yellow Submarine.
My fans know that I’ve won a couple of Grammy awards for Best Pop Male Vocal Performance and sold millions of albums and singles—more than fifty-three million so far. Still, the truth is, very few people know me as well as they know my music, and even fewer know just how much of a crazy, arduous, and rewarding adventure my life has been.
Not many are aware, for example, that my mom had to sign my first record contract for me because I was not quite sixteen years old when it was offered. To have a record deal at such a young age sure seemed like a great running start, but it was only the beginning of a long trek.
You see, I didn’t have a hit record until eighteen challenging years later.
By the end of the 1970s, I was a struggling rock singer, husband, and father of three, facing eviction because my rent checks kept bouncing. If you have keen hearing, you may figure out that I finally found a way to pay the rent by performing scores of jingles for radio and television in the early 1980s for anything from Budweiser beer to Dr Pepper, Subaru cars, and the U.S. Army.
Remember “Be all you can be”? That was me.
Around that same time, I also established myself as a songwriter. I’ve written more than 220 songs, many with co-writers, including Bob Dylan, Lady Gaga, Diane Warren, Desmond Child, Walter Afanasieff, Billy Mann, Kenneth “Babyface” Edmonds, Robert John “Mutt” Lange, Lamont Dozier, and Ne-Yo, among others.
My name appears as a songwriter on records by diverse artists such as Conway Twitty, Kanye West, Jay-Z, KISS, Barbra Streisand, Cher, John Legend, Marc Anthony, Patti Austin, Wynonna Judd, Joe Cocker, Kenny G, Peabo Bryson, Kenny Rogers, Patti LaBelle, Laura Branigan, Gregg Allman, the Pointer Sisters, and many more artists from the country, pop, R & B, and rock genres.
And while I may be known for singing romantic songs about looking for and finding love, anyone who reads the tabloids and gossip sites knows that I’ve made some pretty good runs at romance. Very few people understand how lucky I’ve been in love despite my current single status, but if you keep reading, you will learn that love is still something I believe in very much. You will also gain insight into what it takes to relentlessly pursue and achieve a dream, to endure and learn from failure and disappointment, and to build upon that success over a long and rewarding career.
I’m a million miles from perfect. I’ve made many mistakes and done things—and not done things—I’m truly sorry for; but I have also experienced countless and cherished moments of joy, love, and laughter, and I have no regrets for putting my heart and soul into a career in music—one of the greatest gifts we all can share.
This book is about the soul of it all, which includes the deep emotions and vital forces experienced in a lifetime spent developing gifts and pursuing passions. It’s about recognizing the purpose, the point of it, whether in times of great joy or deep sorrow, in times of sacrifice or celebration. Alexander Pope said, “We are immortal souls in human frames.” I also believe the soul of it all far transcends the human frame. For me, the soul of it all and the true meaning of life are one and the same, and are found in everything from the joy of creating music to treasured moments with loved ones to giving back to others.
I may not know you any more than you know me, but I am confident that reading this story of my journey will not only entertain you but also, I hope, inspire you to persevere in your own quest to achieve your dreams.
There is one more thought I want to plant in your mind before you read my story: I didn’t dream as big as my life has become.
PART I
The Climb
Credit: The Lonely Island
Chapter One
This Is the Tale of Captain Jack Sparrow
Somewhere in my forty years as an artist and performer, I picked up a reputation for being a serious guy.
Many of my fans don’t realize that I was never bar mitzvahed because I was the kid betting on the dreidel in Hebrew class and smoking cigarettes during breaks. If you were beaned by a water balloon or splattered by a flying tomato in Greenwich Village in the 1960s, it was likely launched from the rooftops by yours truly.
You may be surprised to learn that I’m secretly a prankster and a fun-loving kind of guy.
That’s why I did not hesitate when Saturday Night Live’s Lonely Island crew called me to join them in a music video.
Well, maybe I hesitated a little. I mean, these are the guys who convinced Justin Timberlake to put his dick in a box—and sing about it. He was freakin’ hilarious, and of course Justin made it look fun and easy, just as he would any other video.
Justin’s video won a Creative Arts Emmy for outstanding original music and lyrics, and he seemed to enjoy himself doing it. I was a fan of the Lonely Island guys and thought it would be fun working with them, though I worried what they might have me do. As hilarious as Justin’s video was, I found it a little scary to contemplate what they would come up with for me. Justin sang in the Baptist choir as a kid. I sang on crusty street corners for spare change.
The SNL guys assured me they wanted to build a hip-hop song around me singing “a big sexy hook.” They thought I’d be perfect for the job.
Jorm later told an interviewer who asked about my role in the video, “You can’t fake funk like that.”
From the start, Andy, Kiv, and Jorm promised to come up with a shocker skit that people would want to watch again and again, and they did just that.
The next thing I knew, I was in a crow’s nest on a pirate ship decked out like Jack Sparrow, doing Forrest Gump on a park bench, cross-dressed as Erin Brockovich, and flashing my guns as Scarface.
And that was the tamest idea they came up with.
Initially, the mad geniuses of the Lonely Island presented me with a “Lord Boltron” song and video concept that involved violating l
aws of nature and each of the Ten Commandments, repeatedly.
It was hilariously funny, but really, really raunchy.
Now, that’s what I expected from these boys without borders, the creators of family classics such as I Just Had Sex, 3-Way, and Jizzed in My Pants. I loved those videos and the Lord Boltron bit, too. But I was concerned that the proposed Lord Boltron video might slightly upset my fans, because the first script was more than disturbing.
So we met for a creative session in L.A. to try to come up with something not quite so dark but still funny. When we met, I told Andy that my daughters were excited we were working together.
“My mother feels the same way about me working with you,” said Andy.
We hatched out some more ideas for our music video at that meeting. Honestly, they were so busy with SNL and all of their movie and record projects, I didn’t know if I’d ever hear from them again. But over the course of an approximately eight-month period, they somehow found time to come up with a script I could do. When they showed me the final Jack Sparrow concept, I loved it!
We met in New York City for two seventeen-hour days of filming the video. Our locations were the Buddakan restaurant in Manhattan and Brighton Beach, Brooklyn. Andy, Kiv, and Jorma were a pleasure to work with—funny, entertaining, respectful, and thoughtful—despite the tight deadlines. This is a team of guys who collaborated so well on every detail. Andy, Kiv, and Jorm also went out of their way to include me in making decisions. They kept coming up with new twists and gags on the spot. Then they’d run them by me and make sure I was on board, and they had trusted me to ad-lib and stack harmony parts all over the choruses of the catchy little ditty they wrote.
They kept me laughing through the whole process. I think all three of them were shocked when I agreed to a traumatizing scene in which I dressed as Erin Brockovich and breast-fed a doll. Unfortunately, that scene didn’t make the cut. It may have been too over the top even for the Lonely Island team, but I would have voted to keep it.
To my amazement, they had the music video ready for prime time within forty-eight hours. I went to the music video’s premiere on SNL in New York. I was too nervous to sit in the audience, so my manager Christina Kline and I watched from the back of the house. When they introduced our video, I couldn’t breathe until the first waves of laughter came from the audience.
They loved it!
A fellow Connecticut resident, the phenomenal singer, songwriter, and guitarist John Mayer, was on the set when the video premiered. He was certain that it would go viral and become a huge hit.
“People are going to go nuts,” John told me. “They won’t expect this from you, and new fans who don’t even know your music will… well, you’ll see in the morning.”
My daughter Isa, an expert on social media, began monitoring the video’s views on YouTube as soon as it aired. When I walked downstairs the next morning, she looked up at me and said, “You are not going to believe what is going on.” Jack Sparrow was already approaching a million views. She read me comments that included “OMG, I can’t get this song out of my head!”
Just as John Mayer predicted, my music video with the Lonely Island guys went viral and, at last count, had more than ninety million views on YouTube.
Sometimes you have to take risks in life, and this one paid off in a huge way. Ours was the third-most-viewed video on YouTube in 2011, and it received an Emmy nomination, so we were invited to perform it live at the awards show for millions of viewers around the world.
Now I can’t walk through an airport anymore without receiving high fives and fist bumps from eighteen-year-old guys screaming, “Captain Jack Sparrow! Dude, you rock!”
Andy, Kiv, and Jorm, you can call me anytime to do another music video.
So there you have the tale of my latest adventure in a music career that I began seeking at the age of nine while singing in my bedroom closet. What follows is the backstory. You will find many twists and turns—some of them as wild as those in the Jack Sparrow video.
You will also learn about the “soul of it all,” the passion, hard work, striving, sacrifices, joy, and faith it takes to keep the dream alive. It has taken all of that and then some to build and sustain an incredibly rewarding career for more than four decades.
Credit: Marc Friedland
Chapter Two
Finding My Voice
My older brother, Orrin, calls himself “the original Bolton,” which refers to the fact that he was the original rock star of our family. In the early sixties, he worked as a roadie for the Shags, one of the many New Haven bands formed in garages and basements in that musical decade. The Shags were among the few local groups to sign a record deal. A couple of their songs, “Don’t Press Your Luck” and “Breathe in My Ear,” received national radio play. Orrin brought some of the Shags to our apartment when I was ten or eleven. He bragged to them that I could sing.
“Michael may be a scrawny Jewish kid, but he sings like a chain-smoking, whiskey-chugging seventy-year-old black bluesman,” Orrin said proudly.
One of the Shags, Carl Augusto, who played guitar and later taught me basic bar chords, patted my mop of curls and said: “Maybe someday you’ll have your own band, little bro.”
I was four years younger than Orrin and still in elementary school when my brother moved on to playing drums and singing in his own bands. Orrin was an enthusiastic early adopter. The Beatles, the Rolling Stones, and other great bands of the sixties inspired a major cultural shift, leading millions of American male teens to grow their hair longer and form their own groups—and my big brother went all in.
One day he was a high school jock. The next he was a hippie flower child rock ’n’ roll sex god. Women of all ages wanted to sleep with him. Guys wanted to be him. He was a very popular guy, though not with the teachers. My first day of junior high was marred first by kids picking on me for my long hair and second by a teacher whose opening salvo to me was “Don’t think you can get away with everything your brother got away with.”
Orrin was a mysterious figure, even to me and my buddies. He would disappear for weeks and months, then pop up with an exotic beauty on each arm and, at one point, with his eyelids darkened by plant oils he discovered in India.
Upon his return from each of these long absences, Orrin would share tales of adventure in faraway places and show us treasures from his import-export business. My brother was our magical mystery tour guide into the music world, too. Orrin had an anthropologist’s interest in the history of the blues especially. He knew of bands like England’s John Mayall and the Bluesbreakers even before Eric Clapton joined the group. He shared his extensive collection of albums with us, explaining that the Beatles, Stones, and Clapton were actually mining black American rhythm and blues and playing it back to U.S. audiences. Their heroes, he explained, were long-neglected black musicians like Howlin’ Wolf, Robert Johnson, Little Richard, Chuck Berry, B. B. King, John Lee Hooker, and Muddy Waters.
All this was enlightening and inspiring to me, and it didn’t hurt that Orrin’s record collection also included albums featuring Chicago’s Paul Butterfield and Mike Bloomfield—a couple of Jewish guys like me. Orrin and I were known as the first “heads” in our circle of friends. We had long hair and were into the blues before everyone else. It seemed only natural that I would follow Orrin into music, just as I’d followed him into baseball, running, vegetarianism, and martial arts classes. Like him, I was a good athlete, but after our parents divorced, I dropped out of sports.
Instead, I put all of my energy into growing the longest hair of any male in the public school system, playing in bands, and pretending I’d had sex. (“The first time I had sex, it was very scary. I was alone.” Thank you, Rodney Dangerfield.) My mother had custody, but controlling her wild-child sons was another matter. She had her hands full with three willful teens.
I took to the streets, wandering from teen hangouts like My Brother’s Place and On the Green in New Haven, on the fringes of the Yale campus
, to Greenwich Village. Its Bohemian blend of beatniks, painters, poets, and folksingers was then transitioning into the East Coast epicenter for sex, drugs, and rock ’n’ roll.
Well, not so much sex for me, at least not right away. I was barely in my teens when I began wandering the streets of the Village with my brother and older friends. Orrin got all the girls in the early days. Even when I began hooking up with my share of women, I often suspected those who came my way were really after my brother, the legendary charmer. I may have seen myself as the scrawny younger brother with John Lennon wire rims, but I was never in danger of becoming a twenty-year-old virgin.
For the record, I lost my virginity at thirteen to my first cougar. She was all of fifteen and smokin’ hot, but more on that later.
DIVIDED FAMILY
Before we dive into the history of my love life, I should provide some of my family background. Let’s begin with the full disclosure of my true identity: In February 1953—two years behind my sister, Sandra, who was two years behind Orrin—I was born of Russian Jewish heritage into the Bolotin family, pronounced Below-tin. Many years later, I switched out a couple letters and pared it down to Bolton so radio deejays, fans, and telephone operators would have an easier time pronouncing and remembering it.
Orrin took the name Bolton, too, even though he considers it a curse when he is mistaken for his kid brother—unless there is a better seat or a beautiful woman involved. The Bolotins-slash-Boltons always have been an idiosyncratic bunch. Ours was not the Ozzie and Harriet 1950s idyllic familial unit sporting cardigans and kitchen aprons.
We were way ahead of our time: In the ’50s and ’60s, we had all the dysfunctions of the ’70s and ’80s. As I was growing up in New Haven, Connecticut, my childhood and teenage years unfolded on the same schedule as every baby boomer’s, but in that time of social upheaval, the Bolotins were upheaving with the best of them.
The Soul of It All Page 1