Giacomo Gates

Giacomo Gates. (John Abbott photo / November 6, 2013)

The jazz singer Giacomo Gates has taken some roundabout journeys. But they've served him well. He grew up in Bridgeport. Then he moved up to the frozen tundra when he was in his 20s.

"I split from here for like 15 years," says Gates, who spoke to the Weekly recently. "I moved to Alaska for a year and I stayed for 12." Construction work in and around Fairbanks ended up keeping him busy.

As a teenager he'd played in wedding bands in Connecticut, performing music from another era while also listening to the Doors and Marvin Gaye.

"It was the '60s and the '70s," says Gates, "but I was playing music that was written in the '40s."

Gates took a lot of time off from music, "bouncing around" as he puts it. He didn't release his first album until 1992, when he was 42. There was no real clear model for becoming a jazz singer in midlife. "I didn't have a map," says Gates.

One of those not entirely expected and era-jumbling career paths that Gates pursued involved a project featuring the songs of conscious soul proto-rap poet and singer Gil Scott-Heron, who died in 2011.

Scott-Heron is often credited with being one of the creators of hip-hop. His angry, rhythmically packed songs addressed the realities of inner-city life, racial injustice, and political ineptitude in America in the late '60s and the '70s. Scott-Heron's "The Revolution Will Not Be Televised" is a cutting critique of media culture and the way it numbs and blinds us to the grittier truth. You can certainly hear the template for artists like KRS-One and Public Enemy and the Roots in Scott-Heron's music. But there was always more there than just that. Scott-Heron was ambivalent, at best, about being labeled the father of rap. A listen to songs like "Lady Day and John Coltrane" points to Scott-Heron's connection to the jazz tradition, and beyond just in the subject matter: the song's jazzy phrasing and challenging harmonic jumps are more Wayne Shorter than Snoop Dogg.

Gates began discussing the prospects of a record of Scott-Heron's tunes with a producer back in 2006. And the arrangements and recordings were completed, with the finished product ready and scheduled for release in June of 2011. Gil Scott-Heron died in May. It was an unfortunate coincidence. But people were interested in gaining a better understanding of this artist who many giants heaped praises on. And Gates's record, The Revolution Will Be Jazz: The Songs of Gil Scott-Heron, represented a side of Scott-Heron that some people didn't know even existed, showcasing some of the wry, emotional and still-relevant political songs.

"Some of the stuff that he sings — stuff that I really liked — I had no business singing. I'm not gonna sing 'Whitey on the Moon,' or 'Home Is Where the Hatred Is,' because I had no business singing that," says Gates, who is white. "I wanted to sing things that I thought were either funny or really current — like 'Winter In America' is very current."

(One might also consider "We Almost Lost Detroit," not included on the album, as one of those spookily pertinent topical classics.)

The record appeared to be the first tribute album to the great songwriter. It was well received, holding the number-one spot on National Jazz Radio for four weeks. The label was even interested in a second record of Gil Scott-Heron tunes, but Gates, who teaches jazz vocals at Wesleyan University and elsewhere, took on a massive jazz challenge, making Miles Tones, his 2013 record of tunes by or associated with trumpet legend Miles Davis, some of which others had penned lyrics to. (Gates performs tunes from both records this week at the Westport Arts Center.)

Gates also got the chance to write words to Davis's standard "Milestones," not a task that any jazz buff or vocalist would take lightly.

"It's not a nod just to Miles," says Gates of the record, "it's a nod to all the great people who put words to Miles Davis's tunes."

Those lyricists include Oscar Brown Jr., Eddie Jefferson and Jon Hendricks.

And though many listeners are familiar with hearing the instrumental versions of these songs, Miles Davis — like many great jazz soloists — had a singable quality to his playing and phrasing.

"Miles is very lyrical," says Gates. "Miles played the trumpet like he was singing."


Giacomo Gates

Nov. 10, 3 p.m., Westport Arts Center, 51 Riverside Ave., Westport, (203) 222-7070, westportartscenter.org