Legendary crooner Vic Damone died from complications of a respiratory illness on Sunday in Miami Beach, Fla., his daughter Victoria confirmed to the Associated Press. He was 89.

Born Vito Farinola to an Italian family in the Bensonhurst section of Brooklyn, Damone was known for his deep baritone love ballads and Frank Sinatra, whom he idolized and often tried to imitate. Sinatra once described Damone as having “the best pipes in the business.”

After winning a tie on the “Alfred Godfrey Talent Hunt” radio show, Damone’s singing career took off, and the crooner sold millions of records in a recording career spanning over 50 years.

During his performing days, Damone appeared on radio shows, films, television programs, and also sang at nightclubs. However, in his 2009 memoir, “Singing Was the Easy Part,” he said that while singing came easy, being a showman “wasn’t my particular gift.”

Over the span of his career, Damone released over 2,500 records and hit songs like “Again,” ”You’re Breaking My Heart,” ”My Heart Cries for You,” and ”On the Street Where You Live.” He also worked on films like Cary Grant’s “An Affair to Remember,” where Damone sang the theme music.

He continued to perform into his 70s until a stroke in 2002 pushed him into retirement in Palm Beach, Fla., with his fifth wife, fashion designer Rena Rowan.

Damone gave one final performance on Jan. 22, 2011 at the Kravis Performing Arts Center in West Palm Beach to a sold-out crowd.