Red's style of playing cornet was greatly influenced by Bix Beidebecke, but he was a better overall musician and an excellent sight reader. Nichols learned to play music from his father, a college music teacher. After moving east from Utah he teamed up with a Midwestern band called The Syncopating Seven. After that band broke up he moved to New York in 1923. He soon teamed up with the trombonist Miff Mole and the two would go on to make a great many records together under a variety of names such as, Red Nichols and his Five Pennies, Arkansas Travelers, The Red Heads, The Louisiana Rhythm Kings, The Charleston Chasers and Miff Mole and his Little Molers. Usually these sessions featured the same or similar personnel. Red did a series of recordings for the Brunswick Record Company under the name of Red Nichols and his Five Pennies, although the bands were often quite a bit larger. These sessions at first featured trombonist Miff Mole and Jimmy Dorsey on alto and clarinet, and later in the decade featured a who's who of great White Jazz musicians, such as Benny Goodman, Glenn Miller, Jack Teagarden, Pee Wee Russell, Joe Venuti, Eddie Lang, Adrian Rollini and Gene Krupa among others. Red appeared on over 4000 records in the 1920s. Nichols survived the Depression by working in Broadway shows, even leading the pit orchestra for two of George Gershwin's shows; "Girl Crazy" and "Strike Up the Band". In 1934 Red fronted a band for the radio show sponsored by Kellogg's Cereal and led many studio orchestras including one for the Bob Hope Show. In 1959 Hollywood made a highly fictionalized picture of his life called "The Five Pennies", starring Danny Kaye as Red.