The Troy Street Observer

Don Alessi and Guitar Spectacular!

Guitarist Don Alessi, once an ubiquitous presence on Boston’s music scene, was 100 years old when he died on Nov 3, 2018. His prolific career began in the 1940s and blossomed in the 1950s and 1960s. He was everywhere then—in clubs, on records, on radio and television. There was a time when it seemed like you could not pass a day living in Boston without hearing Alessi’s guitar somewhere.

Photo of Don Alessi in 1944
Don Alessi in 1944; trumpet player unknown

Alessi was a jazz man at heart, but he played all styles of music in every imaginable setting. Fred Taylor told me that “Don was the utility infielder of Boston guitarists—whenever anybody came to Boston and needed a guitarist, they called Don Alessi. Any kind of music, he could play it.” On top of his daily radio and TV appearances, trio engagements, and studio work, he backed the likes of Sammy Davis Jr, Tony Bennett, and Jerry Vale. But I’m getting ahead of myself.

Don Alessi owed his first big break to another Bostonian, the bandleader Vaughn Monroe. Monroe organized his first big band in 1940, and based it in Boston during the war years. During that time Alessi was working in the jazz spots around town. The photo of him here was taken at a jam session at the Hop Scotch Room, in the Copley Square Hotel, in 1944. Perhaps someone from Monroe’s band heard him there. Perhaps Vaughn himself did. Someone brought Alessi to Monroe’s attention, and when Bucky Pizzarelli, Monroe’s guitarist, entered the army in late 1944, Don Alessi replaced him. Monroe recorded some of his classic early sides during Alessi’s tenure, including “There, I’ve Said It Again” and “Let It Snow, Let It Snow, Let It Snow.” Pizzarelli resumed his career with Monroe after his discharge, and Alessi returned to Boston.

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