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.

On Radio and Television

Fortune next smiled on Don Alessi in November 1947. Promoter Art Rich plucked him from his gig in a hotel lounge for a jazz concert at Jordan Hall starring cornetist Wild Bill Davison and drummer Baby Dodds. Their dixieland wasn’t Don’s style of music (he favored Charlie Christian), but he played well and earned favorable reviews. Perhaps that led WEEI, the Boston affiliate on the CBS Radio Network, to hire Don for its studio orchestra in January 1948. Or perhaps a good word from Monroe, himself a WEEI veteran, turned the trick. Alessi took to the ad-lib nature of radio, and became a fixture on Carl Moore’s Beantown Varieties morning show.

In 1950, Alessi’s trio was gigging nightly at the Sable Room in the Touraine Hotel. He was plucked from that lounge gig for a slot on local television. The R.H. White department store was about to launch a live daytime show, and the producers needed a band. Don Alessi—affable, good-looking, versatile—was just the guy to lead it. So Don’s trio, with pianist Micky Gentile and bassist Vin Parlay, joined the show on WBZ-TV. I don’t know how long it lasted, but the show established Alessi in the new medium.

Radio and television exposure led to work in Boston’s better clubs, like the Darbury Room and the Latin Quarter, where he could blow some jazz. His recording of “The World Is Waiting for the Sunrise” from about 1953 show him much influenced by Les Paul then. At the Darbury Room he surely encountered Herb Ellis, resident there with the Soft Winds. And to my ears, Alessi’s play is more like Ellis’s than any of the other better-known guitarists.

George Clarke of the Daily Record recounted in May 1954 how Eartha Kitt, playing in the big room at the Latin Quarter, listened to Alessi nightly and loved him. She offered Don a job in her group. He had no interest in the road, though, and declined.

After seven years with WEEI, Alessi moved to WHDH radio in February 1955. WHDH dubbed its crew of studio musicians the Park Squares, after the station’s Arlington Street address. Along with Don Alessi were Bill Green on piano, Lou Magnano on vibes, and Ross Centamore on bass. They worked shows with daytime announcers Ray Dorey and Jess Cain, and later joined them on WHDH-TV, too. They were regulars on Dorey’s Morning Key Club (7 a.m.!), the New England Farm and Food Hour, and finally on Cain’s afternoon program. Cain’s show was a mandatory promotional stop for entertainers coming into Boston, and the Park Squares accompanied all of them, without rehearsal. They were the last of Boston’s radio/television studio bands, and WHDH finally let them go in about 1966.

Alessi on Record

One of Alessi’s first assignments at WHDH paired him with Charlene Bartley, a former big band singer from Los Angeles, on her One to Two program. The two started working together in local nightclubs. Somebody noticed, and RCA signed Bartley to a recording contract. With Alessi alongside, she made the album Weekend of a Private Secretary in 1956. RCA added the percussionist Tito Puente on some tracks, and it turned out to be a fortuitous meeting for Don.

Advertisement for the Don Alessi Trio at the Eliot Lounge, 1968
Don Alessi Trio, Eliot Lounge, 1968

Don Alessi recorded one album as a leader, the Latin-flavored Guitar Spectacular! (Tiffany TR-2020) in 1960. The album included some of the usual titles found on the “X goes Latin” albums of the time, like “Poinciana” and “Besame Mucho.” But there were also less-known pieces, like “Noche de Ronda,” a ballad from 1930s Mexico, and “El Relicario,” a Spanish tune from 1914. The liner notes did not list personnel, but the unmistakable sound of Tito Puente’s timbales drives some of these tunes. I can’t help but think Puente influenced Alessi’s choice of material, too. Was Puente the source of Alessi’s fascination with Latin music? I doubt he acquired it growing up in pre-war South Boston.

In 1967 the Don Alessi Trio, with Magnano and Centamore, began a long, long run in the lounge at the Eliot Hotel, well over 100 mostly consecutive weeks. Alessi interrupted it in late 1967 for a trip to Vietnam with pop singer Connie Francis, to entertain troops in a USO show. That might have been planned by Don Costa, another Boston guitarist and Monroe alumna, who was then Francis’s arranger at MGM.

Things changed for Alessi after 1970, as they did for many of his generation, when the rock wave washed over the world of entertainment. He continued to work through the 1970s and 1980s, often in the company of Magnano or trumpeter Eddie Pizzi, although with less prominence. He worked intermittently with his son Jack, a drummer and vocalist, from the 1960s on. (Jack later formed the vocal group the 3 Swingin’ Tenors with Steve Marvin and Jim Porcella.)

Alessi played publicly as late as 2006, presenting the history of the jazz guitar in neighborhood branches of the Boston Public Library system. I hope the library recorded it, because without a doubt, he knew more about that topic than anyone else in town.

To the music. Here’s one I added to my YouTube channel: “El Cumbanchero,” by the Puerto Rican composer Rafael Hernández. As noted earlier, the Guitar Spectacular! liner notes omit personnel and production credits, but I’m betting it’s Tito Puente playing timbales. Hang on: it’s a wild two-minute ride.