A new Sinatra treasure trove makes the case for AI in music

A new batch of long-buried Sinatra recordings from SING Records lands with real punch, and the AI behind the sound is hard to dismiss

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Frank Sinatra is one of music’s most recognizable names. He’s sold more than 150 million records worldwide in several genres, including jazz, big band and easy listening. He won 11 Grammy Awards in his career, along with one Academy Award (Best Supporting Actor, From Here to Eternity), four Golden Globes, one Peabody Award, four Emmy Award nominations, the Presidential Medal of Freedom and more.

While there’s much we know about Sinatra and his musical legacy, there are many hidden musical gems that have never seen the light of day. Concerts and radio appearances that were never released to the general public. Alternate takes of popular songs buried in the studio archives. Private performances for small audiences quietly (or secretly) recorded for personal use only.

Every so often, these unknown or long-forgotten recordings resurface. Historians and aficionados rejoice in learning about a new treasure trove of Sinatra music. His past work will usually be juxtaposed with the unseen or rediscovered tracks soon to join his entire catalogue. Above all, there will undoubtedly be a greater appreciation and understanding of his skills and talents.

That’s what happened with the man nicknamed “Ol’ Blue Eyes” and “Chairman of the Board,” courtesy of several new recordings released by SING Inc.

SING is a “blockchain IP tech company and rightsholder, selling music from major artists and catalogues as vinyl/digital hybrid releases to mass-market superfans,” according to its official Instagram page. “We tokenize raw content into premium collectible SING Records™, unlocking revenue and consumer data as we lead the return to music ownership.”

There’s a fascinating variety of albums available on SING’s website. Each record and box set contains unique, limited and, in some cases, one-of-a-kind features to attract music collectors and enthusiasts alike. A CD, LP and deluxe recording of Canned Heat’s Live at The Kaleidoscope, for instance. A 180 gram remastered gold vinyl LP of Alex Cuba’s Humo De Tabaco. A deluxe vinyl bundle box containing 54-40’s Green album. A white vinyl, purple vinyl (sold for 24 hours only) and CD release of Wang Chung playing at The El Mocambo in Toronto.

I only became aware of this record company quite recently. After reading Will Friedwald’s Oct. 21 Wall Street Journal review of At the Hollywood Bowl 1943-1948, I decided to reach out to SING. Thanks to Geoff Osler (CEO and co-founder), Sam Ibbotson and Michael Rumeo, I received promo copies of its entire Sinatra catalogue.

What’s my verdict? Each CD and LP is rich, vibrant and contains incredible clarity. Every note, bar and cadence is pristine. It’s almost to the point where you would believe that you’re sitting in front of the blue-eyed Chairman as he’s performing.

“The audio quality of this package is fairly astonishing,” Friedwald wrote in the Wall Street Journal. “It was remastered primarily by Harry Hess in a process that, as annotator Charles Granata told me, used AI and involved treating the voice and the orchestra as separate from each other, then bringing them back together. Although I’m familiar with all of these arrangements, I’ve never been able to hear them with such clarity, such as the piano notes behind the singer on the quieter passages of ‘Night and Day’ as well as the percussion pattern and the guitar part that help ‘What Makes the Sunset?’ sound more like a bolero. The squeals from the crowd take us back to the 1940s, but the quality of the music itself is timeless.”

While my familiarity with these arrangements is obviously different, this assessment made plenty of sense. It’s an example of how AI can be used beneficially and, in the case of Sinatra’s catalogue, enhance our listening and understanding of his musical genius.

Long Ago, Far Away (1943-1951), a deluxe five LP-only box set, is absolutely stunning. The quality of several Second World War broadcasts comes to life in the first few records. Sinatra’s versions of “God Bless America” (his only known recording of the song) and “Speak Low” (which he rarely ever performed) display his familiar range of material, as well as unreleased recordings of “Ol’ Man River” and “She’s Funny That Way” with the Los Angeles Philharmonic Orchestra. There’s also a wide variety of CBS radio recordings in this box set, including an episode of the barely-heard Meet Frank Sinatra with standout performances like “Can’t We Talk It Over” and “There’s No Business Like Show Business.”

Two high-quality albums, At the Hollywood Bowl, 1943-1948 and Christmas on the Air, are also contained in the box set and have individual LP and CD releases. Each version is a bit different from one another. The CDs contain more tracks and, in the case of the latter album, include some intriguing archival footage of station identifications, program introductions and a bit of good-natured humour.

The song selection is exceptional, too. The three Hollywood Bowl concerts have many highlights, including “What Makes the Sunset” and “Night and Day.” As for the Christmas radio programs, there are two exceptional versions of “Jingle Bells” and “White Christmas,” a superb rendition of “Ave Maria” and some great medleys, including one containing “Oh Little Town of Bethlehem,” “Joy to the World” and “Silent Night.”

SING, to its credit, has produced some sensational additions to the Sinatra songbook. The man who famously sang “My Way” would likely be proud of the record company that spotlighted his brilliant work in its own way.

Michael Taube is a political commentator, Troy Media syndicated columnist and former speechwriter for Prime Minister Stephen Harper. He holds a master’s degree in comparative politics from the London School of Economics, lending academic rigour to his political insights.