Phoebe Anne Oakley Moses (1860-1926) starred in Buffalo Bill's Wild West Show, where she astonished the crowds with feats of marksmanship such as shooting the spots out of playing cards. It wasn't long until her audience noticed that the shot-out card looked like a ticket that had been punched by a train conductor. By 1910, the name "Annie Oakley" was not only synonymous with sharp-shooting but with the ticket-playing card connection, and complimentary tickets have been "Annie Oakleys" ever since.
Word History
Etymology
Annie Oakley †1926 American markswoman; from the resemblance of a punched pass to a playing card with bullet holes through the spots