Green’s Dictionary of Slang

small, unimportant, junior, miniature.

1890		Bulletin (Sydney) 2 Aug. 17/2: William was attired in a very ‘pee-wee’ hat and a long ulster, carried in his smashing right hand three presentation walking-sticks, and was followed by a faithful bushman.
1912		Ade Knocking the Neighbors 54: Whenever he ran up behind a Pewee Coffee-Grinder he went into the High and made the Cheap Machine look like a Fish.
1915		O.O. McIntyre New York Day by Day 9 June [synd. col.] She has been engaged [...] to picture plays to be produced by a company of Lilliputians. Archie has called the company the ‘peewee troup’.
1925		Dos Passos Manhattan Transfer 360: Oh we none of us know what we want [...] That’s why we’re such a peewee generation.
1928		C. McKay Home to Harlem 201: That’s the life of a pee-wee cutter, says I. Kain’t see it for mine.
1934		S. Walker City Editor 156: Rarely is there such a thing as too much of a good story. The readers, God help them, have been bored enough by pewee sagas.
1942		P. Wylie Generation of Vipers 90: The peewee caliber of teachers as a class, has reduced our education to a public swindle, an assassination of sanity.
1952		Lait & Mortimer USA Confidential 155: Mickey Cohen, a peewee character, became an eminent citizen.
1969		‘Iceberg Slim’ Mama Black Widow 66: Peewee embers of maroon fire flared in sunken sockets.
1977		(con. 1960s) D. Goines Black Gangster (1991) 76: Find out what peewee gang this kid runs with.
1981		J. Wambaugh Glitter Dome (1982) 118: Zorro Garcia was a peewee member of the Black Spider Gang.
1989		H. Rawson Dict. of Invective (1991) 285: peewee. Small, insignificant.
2023		(con. 1962) J. Ellroy Enchanters 288: [T]he ‘peewee corps’ of the Nite Owl gang [...] a group of boys who pulled house burglaries.