If you caught even a whiff of what was coming through the airwaves in the late 1980s and early ’90s, you probably heard the soulful pop ballads of New Haven native Michael Bolton—“When a Man Loves a Woman,” “How Am I Supposed to Live Without You,” “How Can We Be Lovers.” But few know that Michael’s powerful voice, long silken hair, broad shoulders and musical upbringing have a close analog in the form of a brother four years his senior.
Hearing Orrin Bolton speak about his life is like listening to an un-pop ballad. Traversing American counterculture, international travel and mistaken identity, he jumps from Wayne’s World and bionic briefcases to “the freaky-deaky Dutch” and plugs for cannabis. His mind wanders exciting, eccentric paths, and over the course of his life, so have his feet.
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At 15, Orrin left home and hitchhiked from Amsterdam to the boot of Italy, pretending to be Canadian. At 19, he had his toe broken by a concussion grenade during a protest in Berkeley, California. Later that year he was about eight heads from the rail at Woodstock. Then, with Hendrix and Santana still ringing in his ears, he went to India. 1973 found him in Afghanistan, where he fled Kabul in a midnight taxi during a political convulsion, only to get stranded in New Delhi, penniless, for almost a year.
He’s lived at various times on the coast of Hawaii, the mountainous northeast of Jamaica and the suburbs of Roxbury, Connecticut. But before his whirlwind travels, before his brother’s fame, Orrin was a lanky New Haven teen hopping fences and causing a ruckus.
Orrin and Michael grew up in a Russian-Jewish household in Westville, where both their hair and their last names were longer than they are now. Their mother, Helen Bolotin, who passed away in July, was the musical fount of the family. Orrin, Michael and their sister Sandra grew up on Mom’s favorite show tunes and folk music, along with classic R&B, soul and gospel. So while others in their circle were mumbling through Hebrew prayers, the brothers were belting them for all they were worth.
Their father, George Bolotin, was the chairman of the 24th ward—“a machine politician,” Orrin says, but also a man who earnestly believed a compromise could be a meaningful step forward. Orrin, the son of a more radical decade, wasn’t satisfied with diluted ideals. He befriended students active in Yale’s liberal subculture, protected protestors at rallies, believed strongly in making change outside the system and counted himself among the “hopefuls, radicals, peaceniks, freaks.”
At the age of 14, Orrin played in his first band, the Nomadz. (His brother Michael wasn’t far behind, playing in a band called Joy.) By age 19, Orrin had returned to Amsterdam, where he was the lead singer for the band Jelly Roll Jam. Then, after living—you might say surviving—for two years abroad in Afghanistan and India, Orrin returned to America humbled and emaciated in roughly equal measure. There, he found his brother, Michael, putting his shoulder to the wheel, but without the success he’d hoped for. Seeing his brother’s persistence, passion and talent, Orrin decided to put his own music on hold and lend his own shoulder to Michael’s wheel.
In a burst of efficacy, Orrin started three separate music companies (management, production and publishing) to help promote his brother. He visited 24 record labels before landing Michael his first deal with RCA Records, who was still performing under the family name Bolotin. Then, in 1983—after Michael’s last name was changed to Bolton, which rolled off the tongue more easily—Orrin took some of the political organizing strategies he learned from his father and put them to work building Michael Bolton’s early fan base.
With Michael touring as an opener for Bob Seger & The Silver Bullet Band, Orrin would arrange for attractive girls at each stop to hand out special invitation cards to meet the relatively unknown Michael Bolton face-to-face. Kids lined up in droves at his hotel room, and later conference room, door, where Orrin had them fill out admission forms with their name, address and phone number. He filed away those forms—some 5,000 of them—and whenever Michael returned to a given city, Orrin would call up the kids and tell them where and when his brother was scheduled to arrive. And when Michael did roll in, there’d be crowds of fans waiting for him, conjuring an aura of celebrity before it had truly bloomed.
Of course, Michael’s celebrity eventually did bloom, with vigor. Then, with a sense of accomplishment, Orrin went his own way, preferring to make music than to manage it.
Today, Orrin, who eventually took the name “Bolton” for the same reason as his brother, still performs and puts out new music. In 2011, he released album Liv’n’ Like a Man, whose title song you can find on Youtube, with a new EP presently underway. Orrin—who says he’s still confused for his brother multiple times a day, something he calls being “Michael-waved”—remarks that he occasionally receives condolences from people along the lines of, “I think it’s so terrible when one brother makes it in the music business and one brother doesn’t.”
But Orrin doesn’t see it as a competition. He recognizes that Michael dedicated his life and talents to being a performer, while Orrin committed himself more broadly—to worldliness, spiritual fulfillment and advocating for causes he believes in, with his little brother Michael among them.
Orrin Bolton
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Booking: Shae Jacobson, Exclusive Artist Management. (954) 881-1892 | eam2008@yahoo.com
Written and photographed by Daniel Shkolnik.
