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=== Brunswick Records era === Nichols could read music and easily gained studio work. In 1926, Mole and he began recording with a variety of bands as Red Nichols and His Five Pennies.<ref name="LarkinJazz"/> Few of these groups were quintets; the name was a pun on "nickel".<ref name="LarkinJazz"/> With the Five Pennies, he recorded more than 100 sides for Brunswick. He also recorded as the Arkansas Travelers, the California Red Heads, the Louisiana Rhythm Kings, [[the Charleston Chasers]], Red and Miff's Stompers, and Miff Mole and His Little Molers. During some weeks in this period, Nichols and his bands were recording 10 to 12 two-sided records. Nichols' band started with Mole on trombone and [[Jimmy Dorsey]] on alto saxophone and clarinet.<ref name="LarkinJazz"/> Other musicians in his bands in the following decade included [[Benny Goodman]] (clarinet), [[Glenn Miller]] (trombone), [[Jack Teagarden]] (trombone), [[Pee Wee Russell]] (clarinet), [[Joe Venuti]] (violin), [[Eddie Lang]] (banjo and guitar), and [[Gene Krupa]] (drums).<ref name="LarkinJazz"/> The Five Pennies' version of "Ida, Sweet as Apple Cider" was a surprise hit record. It sold over a million copies and was awarded a [[music recording sales certification|gold disc]] by the [[Recording Industry Association of America]].<ref name="The Book of Golden Discs">{{cite book| first=Joseph| last=Murrells| year=1978| title=The Book of Golden Discs| edition=2nd| publisher=Barrie and Jenkins| location=London |page=[https://archive.org/details/bookofgoldendisc00murr/page/136 136]| isbn=0-214-20512-6| url-access=registration| url=https://archive.org/details/bookofgoldendisc00murr/page/136 }}</ref> His composition "Nervous Charlie Stomp" was recorded by one of the top jazz bands of the 1920s, [[Fletcher Henderson]]'s orchestra featuring [[Coleman Hawkins]] on sax, and released as a 78 single. In the next decade, more structured [[swing music|swing]] eclipsed the improvisational hot jazz Nichols loved to play.<ref name="LarkinJazz"/> He tried to follow the changes and formed a swing band, but his recording career seemed to stall in 1932. Music critic Michael Brooks wrote, <blockquote> What went wrong? Part of it was too much, too soon. Much of his vast recorded output was released in Europe, where he was regarded by early jazz critics as the equal, if not the superior, of Louis Armstrong and [[Bix Beiderbecke]]. People who make fools of themselves usually find a scapegoat, and when the critics were exposed to the music of [[Duke Ellington]], [[Benny Carter]], [[Coleman Hawkins]], and others, they turned on Nichols and savaged him, trashing him as unfairly as they had revered him. Nichols' chief fault was an overly stiff, academic approach to jazz trumpet, but he did recognize merit as far as other jazz musicians were concerned and made some wonderful small-group recordings.<ref>Michael Brooks, liner notes to ''Swing Time! The Fabulous Big Band Era 1925β1955''.</ref> </blockquote> Other labels Nichols recorded for included [[Edison Records|Edison]] 1926, [[Victor Records|Victor]] 1927, 1928, 1930, 1931 (individual sessions), [[Bluebird Records|Bluebird]] 1934, 1939, back to Brunswick for a session in 1934, [[Variety Records|Variety]] 1937, and [[Okeh Records|OKeh]] in 1940.
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