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=== 1927β1929: Early career === In 1927, Calloway joined his older sister, [[Blanche Calloway]], on tour for the popular black musical revue ''[[Plantation Days]]''.<ref name=":6" /> His sister became an accomplished bandleader before him, and he often credited her as his inspiration for entering show business.<ref>{{Cite web|last=Lloyd|first=Robin|title=Black History Month: The Bold Blanche Calloway|url=https://www.knkx.org/post/black-history-month-bold-blanche-calloway|access-date=March 26, 2021|website=www.knkx.org|date=February 25, 2021|language=en}}</ref> Calloway's mother wanted him to be a lawyer like his father, so once the tour ended he enrolled at [[Crane College]] in Chicago, but he was more interested in singing and entertaining. While at Crane he refused the opportunity to play basketball for the [[Harlem Globetrotters]] to pursue a singing career.<ref name=":1" /> Calloway spent most of his nights at β[[Black and tan clubs]]β such as Chicago's Dreamland CafΓ©, [[Sunset Cafe]], and Club Berlin, performing as a singer, drummer, and master of ceremonies.<ref name=":6" /> At Sunset Cafe, he was an understudy for singer [[Adelaide Hall]]. There he met and performed with [[Louis Armstrong]], who taught him to sing in the [[Scat singing|scat]] style. He left school to sing with the Alabamians band.<ref name="Ossman">{{cite news |last1=Ossman |first1=David |title=Cab Calloway: 'A Hi De Ho Centennial'|url=https://www.npr.org/2007/12/26/17408371/cab-calloway-a-hi-de-ho-centennial|newspaper=NPR.org |access-date=June 16, 2021}}</ref> In 1929, Calloway relocated to New York with the band. They opened at the [[Savoy Ballroom]] on September 20, 1929. When the Alabamians broke up, Armstrong recommended Calloway as a replacement singer in the musical revue ''[[Connie's Hot Chocolates]]''.<ref name=":6" /> He established himself as a vocalist singing "[[Ain't Misbehavin' (song)|Ain't Misbehavin']]" by [[Fats Waller]].<ref name=":7">{{Cite magazine|date=August 14, 1993|title=Catchin' Cab: The Magic of Calloway|url=https://books.google.com/books?id=6BEEAAAAMBAJ&q=cab&pg=PA61|magazine=Billboard|page=3}}</ref> While Calloway was performing in the revue, [[The Missourians (band)|the Missourians]] asked him to front their band.<ref>{{Cite book|last=McClellan|first=Lawrence|url=https://books.google.com/books?id=Oit7y0bS4MUC&q=savoy+cab+calloway+1929&pg=PA90|title=The Later Swing Era, 1942 to 1955|date=2004|publisher=Greenwood Publishing Group|isbn=978-0-313-30157-5|page=90|language=en}}</ref>
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