NEW YORK (AP) - Fred Milano, who made rock and roll history on doo-wop hits with Dion and the Belmonts in the 1950s and appeared at the Legendary Surf Ballroom in Clear Lake, Iowa, with Buddy Holly, has died. He was 72.
Milano, who died Sunday in New York, continued to perform while starting a late-in-life career with the New York City Department of Correction.
Milano, as a member of the Belmonts, appeared on a slate at the Surf with Holly, J.P. "The Big Bopper" Richardson and Ritchie Valens the night the three died in a plane crash just shortly after takeoff, on Feb. 3, 1959.
"With everyone who loves the roots of Rock 'n' Roll, I'm mourning the loss of Freddie Milano. Fred played an important role in my younger life," said Dion DiMucci, lead singer for the Belmonts in their early years.
In an email to the Globe Gazette, DiMucci said, "I will always remain grateful for his contribution in 1958 & 59 - may he rest in peace and rock on in heaven."
Milano appeared with the Belmonts in Clear Lake during Winter Dance Party celebrations, most recently in 2007, 2008 and 2009.
Milano died three weeks after he was diagnosed with lung cancer, said Warren Gradus, who joined the Belmonts in 1963. Milano lived in Massapequa, on Long Island, and died in a hospital, Gradus said.
Milano and three friends from the Bronx formed the Belmonts in the mid-1950s, borrowing their name from the borough's Belmont Avenue. They became Dion and the Belmonts after DiMucci joined in 1958.
Milano sang tenor on hits like "A Teenager in Love" and "Where or When."
DiMucci in an interview recorded in 2009 and shown at last year's Winter Dance Party's Iowa Rock and Roll Hall of Fame, recalled an incident during the Winter Dance Party Tour in 1959, when Milano, fascinated by a handgun carried by Holly, purchased one of his own in Iowa.
He did not know much about guns, but Milano's purchase, according to DiMucci, became important the day after the crash that killed Holly.
When a Moorhead, Minn., theater manager wanted to deduct $450 from his $600 payment to the tour because three of the stars "did not show up," Milano pulled out the gun.
"He (Milano) made him an offer he couldn't refuse," according to DiMucci. Tour members got their money.
The Belmonts continued to perform and to record with different lineups after DiMucci left for a solo career. Gradus said Milano was performing with the Belmonts at casinos and other venues just weeks ago.
There was strife between DiMucci and Belmonts members, who were not pleased when DiMucci was inducted into the Rock and Roll Hall of Fame without them in 1989.
DiMucci said Milano "was very savvy with harmonies" and added, "We had our ups and downs through the years but that's how things go in families, even rock-and-roll families."
Milano went back to school in middle age and joined the Department of Correction in 2003.
In his position as a legal coordinator at the Rikers Island jail complex, he helped inmates research their cases and taught a legal research class, said Karen Powell, director of law libraries for the department.
Powell said Milano had more energy than colleagues two decades younger and "was a person who really loved life."
"We'd know it was him coming through the door because we'd hear him singing and skipping up the stairs," Powell said.
Milano is survived by his wife, Lynn, two children and 10 grandchildren.
Globe Gazette Assistant City Editor Deb Nicklay contributed to this report.