In 1929, the rapid rise in the radio popularity of Rudy Vallee prompted Osborne to add his own vocals to his recordings.

[3] In his book, The Big Bands, George T. Simon noted that the tenor of the times contributed to Osborne's early success: "Then in 1929 came the stock-market crash and the Depression.

The search for security, for sweetness and light, was reflected in the country's musical tastes — in its acceptance of crooners like Rudy Vallee and Will Osborne, and then Bing Crosby and Russ Columbo, in its preference for dance music that encouraged romance and sentiment and escape.

"[4] Simon described the band that Osborne formed in 1935 as "a stylized outfit that featured rich, deep-toned brass, emphasizing, of all things, trumpets plus glissing trombones blown through megaphones.

A 1948 newspaper article reported that, at that time, "The band holds the all-time attendance record at Palomar Ballroom in Los Angeles.