Its always about the next song
Peter Diamond “The most important thing is always the next song.”

Peter Diamond Ilacqua was born in central New York near Syracuse. At age 6, he moved to Key West to live with his father. Peter graduated from Key West High School in 1961. He later went to school in Miami and became a hairstylist. Peter recalls that everyone loved Jimmy Buffet when he first started to play in Key West in the 70s, but that he was upstaged once in a while by a folksinger named Elizabeth Corrigan.
The only time Peter has been off the “Rock” was in 1979 when he moved to a wonderful music community in Maui, Hawaii. He spent 9 years there and became inspired to sing when he returned to Key West.
Peter returned to Key West in the mid 80s. He remembered the Key West sound during the late 50’s through the 70’s to be dominated by what he termed the Hammond organ beat lead. Key West had musicians like Alan Wallace (the best tenor saxophone player), Harry Chip Chase, and vocalist Cliff Sawyer. He said the best singer that he ever heard in Key West was Daniel Acosta. His favorite Key West drummer was Bobby Adrian who was from England and was the first drummer for the Beatles. Peter began singing with Tim McAlpine who influenced his musicality and performances.
Peter is an accomplished hairstylist by trade and when he returned to Key West, he worked for a short period at the then famous Moe’s Barbershop Hairstyling located at 609 Duval Street. At the time Moe’s was the center of local street life, where deals were brokered, ideas argued, and always full of local celebs. It was a huge classic conch downtown social scene. Peter emceed the proceedings while he sang and cut hair.
Of the many Key West musicians, I have interviewed, Peter was the first to tell me about Coffee Butler. To Peter, the legendary Coffee Butler was the only true superstar from Key West. Butler could sing and entertain like Louis Satchmo Armstrong and had a charming personality. Peter told about Coffee’s athletics as an outstanding shortstop at William Douglas High School and had tried out for the Kansas City Monarchs in the old Negro League.
After baseball and a stint in the Army, Coffee returned to Key West and entertaining. Coffee Butler played at the Hukilau, a dinner club on North Roosevelt for almost twenty years. These stories inspired me to meet and interview Coffee Butler. I coaxed him out of retirement and produced five sold out performances at the Key West Theater. Coffee and I became great friends. Many thanks to Peter Diamond for the inspiration.
Longtime Key West musician, Skipper Kripitz identified Peter Diamond as “our resident Sinatra swinging vocalist.” According to Skipper, Peter is the “the living embodiment of the classy, dancing, jazzy aspects of this town for many decades.” He went on to say that Peter was like a big brother figure to him, always beloved.
Larry Smith met Peter when he first moved to Key West in 1991. He and Peter became great friends and helped each other tremendously. One evening in early 1992, Peter was singing the jazz standard, “You Are Too Beautiful” at La Te Da. During the song, he asked a lady in the audience, named Holly, to dance. They danced like they had rehearsed together for years. After a little coaxing by Larry, they started dating and were dancing together as husband and wife until Holly passed in 2021.
“They were the Fred Astaire / Gingers Rogers of Key West” said Skipper Kripitz. They were the classiest couple with the best dance moves, always impeccably dressed and obviously truly in love. Larry Smith considered Peter and Holly as family and wrote a tribute song titled “Holly Angel”. It was performed by the Paradise Big Band in 2022.

Peter gives a great deal of credit for the growth of the Key West music scene to the club owners who could “feel the music” and really cared about the performance and sound. He recalls names like Dante Capas, owner of Two Friends, Carmelo Vitale, owner of Virgilio’s, Danny Knowles of Captain Hornblower’s, Charlie Bauer of Smokin’ Tuna, and Mark Rossi’s Rick’s/Durty Harry’s complex.
Peter feels that John Vagnoni, of the Green Parrot, knows more about being a musician than any other owner. He understands the music scene and the musician’s life. Some owners consider musicians just necessary. He says that John understands the dynamics and difficulties of music and being a musical performer. He seems to appreciate musicians’ work, compliments their performance, and is glad to pay them for their music.
Over the years, Peter has developed a fine repertoire of songs and very good style of performance. His simple philosophy is “it’s easy to be beautiful … more difficult to be interesting,” and to Peter the most important thing is always about the next song.

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