Luisa Tetrazzini & Attilio Baggiore - PICCOLO AMORE (recorded 1922; released c. 1980 on Rococo Records LP 5361)
The oldest U.P. GROOVE of which I'm aware was recorded in September 1922 and featured Calumet-born operatic tenor Attilio Baggiore.
During the early 1920s, Baggiore was the protege (and probable lover) of the much-older Luisa Tetrazzini, one of the greatest divas of the early 20th century. In September 1922, Tetrazzini made 15 recordings in the studio of The Gramophone Company Ltd. in Middlesex, England (they would be her last studio recordings); two of these were duets with Baggiore. Some of these were made for The Gramophone Company to release; some were intended for (pre-RCA) Victor.
Unfortunately, neither The Gramophone Company nor Victor considered these sides worthy of release, and the metal masters were destroyed. Happily, Tetrazzini kept her own copies of all but one of these tracks, and they were finally released circa 1980 by Rococo Records, a small Canadian company.
Sadly (for us), the one track Tetrazzini couldn't save was one of her duets with Baggiore, a duet from Verdi's RIGOLETTO. But their performance of Lama's "Piccolo Amore" made it to our day. Since its release on Rococo, it's been put out on two multi-CD collections of Terazzini's complete recordings.As for Baggiore, he continued his career and became a highly-regarded tenor in both Italy and America; he toured the US as part of the "National Male Quartet," and sang several times on US radio in the 1930s - he may have even appeared on some early TV programs. But, incredibly, he never made another commercial recording after his time with Tetrazzini!
(Most of the above Baggiore info came from the book LUISA TETRAZZINI: THE FLORENTINE NIGHTINGALE by Charles Neilson Gattey [Amadeus Books, 1994].)