Legendary crooner Vic Damone, whose hits included “You’re Breaking My Heart” and “On the Street Where You Live” and who had roles in film and TV, died Sunday at a Miami Beach hospital from complications of a respiratory illness, his daughter Victoria told The Associated Press. He was 89.

Inspired by his favorite singer Frank Sinatra, Damone began his more than half-century career as winner of Arthur Godfrey’s Talent Search in 1947, leading to his becoming a regular on the show. His first release, “I Have but One Heart”, reached No. 7 on the Billboard chart. “You Do” reached the same peak. These were followed by a number of other hits, including 1949’s “You’re Breaking My Heart”, which went gold, and 1955’s “On the Street Where You Live.”

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He segued into acting as well in the 1950s, appearing in films The Strip, playing himself, and Rich, Young and Pretty. He also had major roles in the movie musicals Hit the Deck and Kismet (right). Moving into television, he hosted for a short time his own show The Vic Damone Show in 1956, which aired as a summer replacement for December Bride. The show featured Damone singing with many of his friends as guests.

His other TV work included the role of Stan Skylar in the 1960 “Piano Man” episode of CBS’ The DuPont Show with June Allyson and Jess Wilkerson in the 1961 episode “The Proxy” of ABC’s The Rebel, starring Nick Adams. He also played the crooner Ric Vallone in the 1962 episode “Like a Sister” of CBS sitcom The Dick Van Dyke Show. In the summers of 1962 and 1963, Damone hosted another a television variety series on NBC called The Lively Ones, which showcased current jazz, pop and folk performers, as well as comedians.

In the early 1970s, Damone went through a rough stretch, having to declare bankruptcy, but started touring Las Vegas casinos as a performer and earned enough to clear up his financial difficulties.

In 1972, he was offered the role of Johnny Fontane in The Godfather. The role ultimately went to Al Martino. Damone had turned down the role for several reasons, reportedly because he felt it did not have enough screen time or paid enough but also due to a fear of provoking the mob and Sinatra, whom Damone deeply respected.

One of his final public performances was on January 19, 2002, at the Raymond F. Kravis Center for the Performing Arts in Palm Beach, FL. Damone suffered a stroke the same year and subsequently retired. His final album also was released that year.

Damone also was a personal friend of Donald Trump. In May 2016, Trump offered to be a character witness on Damone’s behalf in the event of any legal action his step-daughters may take to prevent him from receiving any of his then-ill fifth wife Rena Rowan’s estate, worth an estimated $900 million.