Green’s Dictionary of Slang

1. (US) a free pass, orig. to a circus, but latterly to the theatre.

1914		Monitor 1-2 20/1: Next time we want ‘Annie Oakleys’ we'll walk right up to the box office and tell the man we know Jerry Flood.
1916		T.A. Dorgan in Zwilling TAD Lex. (1993) 14: One-Eyed Connelly never paid to see a fight in his life [...] He either got an Annie Oakley from a friend or was passed in with one of the principals.
1924		O.O. McIntyre New York Day by Day 14 Dec. [synd. col.] Complimentary tickets – known as ‘Annie Oakleys’ – are punched with rifle-like holes.
1925		Sportsman-Rev. (Spokane, WA) 2 Aug. 17/1: ‘And me with a ringside seat without no Annie Oakley punched in it’.
1931		Irwin Amer. Tramp and Und. Sl. 19: Annie Oakley. — A free ticket or pass to an amusement or entertainment.
1948		C.S. Montanye ‘Crepe for Suzette’ Thrilling Detective Oct. 🌐 Libby had a pair of Annie Oakleys in her handbag — the reason for the taxi and the ice show.
1962		Ragen & Finston World’s Toughest Prison 789: annie oakley – A free ticket or pass.

2. (US Und.) a pardon or discharge certificate given to a convict.

1949

Monteleone Criminal Sl. (rev. edn).