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Bobby Milano: 1936-2006
Bobby Milano
singer

Born: 1936 in Buffalo, NY
Died: January 17, 2006 in Rancho Mirage, CA

Crooner and producer

by Todd S. Jenkins
Copyright © 2006 Todd S. Jenkins

Entertainer and producer Bobby Milano, a longtime fixture of the Palm Springs area, died of liver cancer at Eisenhower Medical Center in Rancho Mirage, California, on January 17, 2006. He was sixty-nine years old.

Born Charles Caci in Buffalo, New York, Bobby Milano’s career began when he won the “Ted Mack Amateur Hour” competition at the age of twelve. He made his first record at sixteen, and headed to Los Angeles in 1955 to build his career in the entertainment business. He continued to make occasional records, including a popular single called “Life Begins At Four O’Clock” (Challenge). Later he signed with Capitol Records, but his career was cut short by the advent of rock ‘n’ roll in the late 50s. He then became embroiled in the Southern California underworld, earning the nickname “The Crooning Crybaby” after an ugly run-in with the law. Caci/Milano was convicted in 1968 for complicity in jewel theft and transportation of stolen goods.

Following his conviction, Milano transcended his sordid past and resumed the straight path, thanks in large part to his loving wife, vocalist Keely Smith. Milano produced a number of records for Smith in the second phase of her career, well after her heyday with first husband Louis Prima. In the 1970s Milano and Smith moved to Palm Springs, California, where Milano maintained his home ever since.

Milano was a frequent fixture at nightclubs all across the Coachella Valley. He recorded a big-band album under the direction of Dennis Michaels, but the record was never released. Despite being bypassed by real success, Milano built up a large, loving cadre of friends, family and business associates. Singer Kenny Colman said Milano “was a great friend to me and to many. Bobby could sing with gusto and feelings. If you were lucky enough to hear him, he had chops unlimited!” Milano was diagnosed with cancer in November 2005. Despite his advancing illness, he performed at a New Year’s Eve party at Tony's Pasta Mia in Palm Springs, hosting longtime friends like Frankie Avalon and Jerry Vale.

Bobby Milano is survived by his companion, Betty Battista; daughter Jill Caci of Palm Springs; sisters Leto Concetta and Clara Marranca of Buffalo, New York; brother Vincent “Jimmy” Caci of Palm Springs, and cousin Mike Costley of Palm Desert.


Todd S. Jenkins
Todd S. Jenkins is a member of the JJA, author of Free Jazz and Free Improvisation: An Encyclopedia (Greenwood Press, 2004) and I Know What I Know: The Music of Charles Mingus (Praeger, 2006), and a contributor to Down Beat, All About Jazz, American Songwriter and Route 66 Magazine.

E-mail: Epistrophy@aol.com

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