Ted Weems & His Orchestra were among the most popular attractions on the Midwest music circuit throughout the period separating the two World Wars, earning their greatest success with the novelty hit Piccolo Pete. Ted Weems organized his first band in 1922 with the aid of his trumpeter brother Art Weems. The orchestra moved to Chicago in 1929, and the Windy City remained its primary base of operations throughout its lengthy career.

In 1935 the band welcomed a then unknown Perry Como, who remained their featured vocalist until 1941.