Her first known publicized performance was singing with the studio band of Radio WOWO, Fort Wayne. She worked at various clubs in Indiana, including the Chateau Lido in Indianapolis. From there she moved to North Omaha, Nebraska, where she sang and played guitar for a variety of territory bands, or groups whose touring activities and popularity were geographically limited to several adjoining states, that were led by Red Perkins. During that time Winburn was a collaborator of Lloyd Hunter, frequently singing for Lloyd Hunter's "Serenaders". She also led the Cotton Club Boys out of Omaha, a group that at one point included the amazing guitarist Charlie Christian. When many of the musicians were lost to the World War II draft, Winburn joined the InternationalSweethearts of Rhythm. Soon she went to Oklahoma City and led bands for a short while. It was there that she led Eddie Durham's "All-Girl Orchestra", which eventually earned her an invite to join the International Sweethearts of Rhythm.
International Sweethearts of Rhythm
had been the composer for the International Sweethearts of Rhythm for two years before leaving to join Count Basie's band. After being recommended by Jimmie Jewel, who owned North Omaha's Dreamland Ballroom, Winburn became the leader of the band in 1941. She was reportedly hired for her attractive figure, with the intention of doing little actual composing or singing. In the 1986 documentary film International Sweethearts of Rhythm, Winburn reported of her first meeting, "I said 'What a bunch of cute little girls, but I don't know whether I could get along with that many women or not.' " Despite rumors of Betty Carter being groomed to take her place after her marriage, Winburn was the leader of the band until it folded in late 1949. Winburn formed other incarnations of the International Sweethearts for the next 10 years, often billing her name before the band's. However, those bands never regained the notoriety of the early years. Anna Mae Winburn and Her Sweethearts performed at the eighth Cavalcade of Jazz concert held also at Wrigley Field which was produced by Leon Hefflin Sr. in Los Angeles on June 1, 1952. Other featured artists were Jerry Wallace, Toni Harper, Roy Brown and His Mighty Men, Louis Jordan, Jimmy Witherspoon, and Josephine Baker.
Family
Anna Mae Winburn was born in Port Royal, Tennessee, to Andrew Jackson Darden and Lula Carnell '', a musical family. Her family moved to Kokomo, Indiana, when she was young. She was the fourth oldest of 9 siblings – five brothers and three sisters:
Lloyd W. Darden
Gus Darden
Matilda "Mattie" Ruth Darden
Carnell Andrew Darden
Easter Marie Darden
James Edwin Darden
Julia "Judy" Mae Darden
Morris Briggs Darden
Marriages
On January 2, 1930, Anna Mae Darden married Charles Winburn in Howard County, Indiana. In 1947, Anna Mae Winburn was granted a divorce by the Howard CountyCircuit Court in Kokomo. In the divorce proceedings, she testified that Charles abandoned her in June 1934. Around 1948, Winburn married "Duke" Pilgrim around 1948. They had four children. They lived in Elmhurst, New York, among many Harlem transplants and jazz greats. Duke Pilgrim, before marrying Anna Mae, had been divorced from Albertha Adams '', a dancer whom he married April 27, 1940, in Manhattan.