According to the great jazz singer and blues shouter Jimmy Rushing, it was the advent of sound system technology that changed the singing style of vocalists appearing with jazz or blues groups. Rushing's generation, which included performers such as Big Joe Turner and Jimmy Witherspoon, had figured out how to get their voices over the top of the band, rhythm section, and all, without the benefit of amplification because there was none available. The advent of the megaphone brought about crooners such as Rudy Vallee, yet this device had such a limited sound it was in turn not suited to every type of performance. It was the invention of the microphone around 1933 that made it possible for singers such as Orlando Roberson or the Jimmie Lunceford band's Dan Grissom to be heard over the sound of a full band. Once they did, the effect on the listening public was devastating, paving the way for the likes of Frank Sinatra and Perry Como.

Vocalists such as Roberson were often considered showstoppers, not only because of their vocal range, but because audiences were not used to hearing voices such as his coming from the bandstand. The voice of Orlando Roberson is most frequently described as high, with some listeners even assuming it is a woman singing. He was part of the first wave of the type of fragile, subtly expressive voices that were indeed made possible by microphone technology. As a result, vocalists could have the same time of musical flexibility as instrumentalists. He has often been misidentified as Orlando Robeson, a spelling difference of one letter which has also led to the misconception that there was a family relation to the great gospel and dramatic singer Paul Robeson. In reality, the two are not related other than their choice of careers. Orlando Roberson's sister Ida Mae Roberson is the only member of his family to have any notoriety. She was one of the face-saving "wives" of the gay poet Countee Cullen, who published some ten volumes of work.

He is most often associated with the bands of Claude Hopkins, a pianist whose ambitious arrangements were often scuttled by the ineptness of some of his sidemen. The bandleader recorded steadily between 1932 and 1935, and much of this material has been reissued on three Classics compact discs. The trumpeter and vocalist Ovie Alston was also part of the Hopkins lineup, frequently sharing the vocal duties with Roberson. Other members of this group included trombonist Fernando Arbello, youthful clarinetist Edmond Hall, and tenor saxophonist Bobby Sands. The most complete glimpse of the singer and this band in action is provided by several short films released by Vitaphone in the mid-'30s, which later became part of the United Artists collection. #By Request, directed by Roy Mack, is set in a nightclub and features the Hopkins orchestra with Roberson vocalizing and the dancers Tip, Tap and Toe. The songs packed into the film's 11-minute running time include California, Here I Come, Chasing My Blues Away, Chinatown, My Chinatown, I Would Do Anything for You, A Quarter to Nine/Shine, and To Call You My Own. #Barber Shop Blues may sound like a lament from the hippie era, but was actually a 1933 short in which the talented Four Step Brothers join Hopkins and Roberson to perform Loveless Love, Nagasaki, and several other tunes. Roberson also performed and recorded with Fats Waller, Edgar Hayes, and Ben Selvin. ~ Eugene Chadbourne, Rovi