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Arthur Prysock straddled two different eras, emerging during the twilight of the baritone big-band singers and making a run at the charts during the rise of soul music in the late '50s and early '60s. Ace's 2014 compilation Too Late Baby: The Old Town Singles 1958-66 chronicles this phase, which arrived after he had several singles for Decca, but before he settled into a role as a jazz singer with a series of albums for Verve in the late '60s. This means his stint at Old Town Records, the New York-city based soul and R&B label, was indeed transitional, finding the elegant vocalist easing into standards that were straight in his wheelhouse but also tackling jump blues, splashy supper club material, and straight soul. No matter the setting, Prysock sounds like himself -- robust, strong, classy, masculine, the bridge between Billy Eckstine and Lou Rawls -- which is a blessing and a curse. When the material is a little bawdier, as it is on versions of "I Just Want to Make Love to You" and Roy Brown's "Good Rockin' Tonight," Prysock's inherent smoothness feels out of place, but he fares better with the ebullient uptown rhythms of "One More Time," a song that walks the line between adult and adolescent audiences. That record reached 30 on the R&B Singles chart in 1961 and, four years later, he had his biggest hit with the slow-burning "It's Too Late, Baby Too Late," a single that existed right at the cusp of jazz and soul. Both of those singles are here, along with 22 other selections (most make their CD debut; Prysock's catalog never received much digital attention), and the compilation is a snapshot of the shifting tides of adult-oriented black pop, hearing how it slowly shifted from nightclub standards to softer soul and, eventually, landing on a jazz informed by soul but not belonging to it. As such, Too Late Baby is interesting as period soul but it also demonstrates that no matter the setting, Arthur Prysock was a consummate vocalist.