From his earliest career, Russell's style was distinctive. The notes he played were somewhat unorthodox when compared to his contemporaries, and he was sometimes accused of playing out of tune. By the mid-1920s Russell was a sought-after jazz clarinetist and worked with Jack Teagarden in pianist Peck Kelly's band in Texas. Back in St. Louis, Russell played with Frankie Trumbauer and Bix Beiderbecke at the Arcadia Ballroom, which had hired Trumbauer as bandleader for the season spanning September 1925 and May 1926. For a short while, Jack Teagarden also played at the Arcadia, and Russell claimed that this was the greatest band he had ever played in. In 1926 he joined Jean Goldkette's band, and the following year he left for New York City to join Red Nichols. While with Nichols's band, Russell did frequent freelance recording studio work, on clarinet, soprano, alto and tenor sax, and bass clarinet. He worked with various bandleaders (including Louis Prima) before beginning a series of residences at the famous jazz club "Nick's" in Greenwich Village, Manhattan, in 1937. He played with Bobby Hackett's big band, and began playing with Eddie Condon, with whom he would continue to work, off and on, for much of the rest of his life – though he complained, "Those guys Nick's and Condon's made a joke, of me, a clown, and I let myself be treated that way because I was afraid. I didn't know where else to go, where to take refuge".