Green’s Dictionary of Slang

1. the penis, usu. of a small boy [pee-wee v.].

1890–1904		Farmer & Henley Sl. and Its Analogues.
1970		E. Thompson Garden of Sand (1981) 280: He sat there with a peewee hard-on, secretly mashing it.
1974		J. Lahr Hot to Trot 114: Keep your peewee out of me.

2. (Aus.) a bowler hat.

1895		Truth (Sydney) 17 Mar. 1/8: The New Woman will wear a ‘hard-hitter’ or a ‘pee-wee’ hat and baggy breeches and cowhide boots.
1951		D. Stivens Jimmy Brockett 30: We wore bell-bottomed pants, bum-freezer coats, pee-wee hats and high-heeled boots.

3. (drugs) a very thin marijuana cigarette.

1970

C. Major Dict. Afro-Amer. Sl.

4. a nickname for any noticeably small or short person.

1919		F. Hurst ‘Even As You And I’ in Humoresque 270: Little peewee, you!
1931		P. Stevenson Gospel According to St Luke’s 22: He looks like a first-former. Sickly, anaemic-looking pee-wee. The new kids call him Ethel!
1943		W. Guthrie Bound for Glory (1969) 416: Hay, dere, Pee Wee. You’n me’d betta unload.
1949		Yorks. Post 29 Nov. 3/8: Empire Leeds [...] Harry lester and His Hayseedsa (Goofus Bob Lester Pee-Wee Pete).
1954		(con. 1937) C. Chessman Cell 2455 87: You don’t like it, huh, peewee?
1974		J. Lahr Hot to Trot 133: How can you have the bad taste to love that lard-ass creep, that Protestant peewee?
1986		R. Fitzgerald Pushed from the Wings (1989) 151: Looks like you need a drink, peewee.

5. (US drugs) crack cocaine, esp. $5 worth (i.e. very little).

2001

ONDCP Street Terms 16: Pee Wee — Crack Cocaine; $5 worth of crack.

6. (UK black) a very junior member of a gang.

1969		(ref. to 1950s) R.L. Keiser Vice Lords 6: Each branch was subdivided into age groupings called ‘Seniors,’ ‘Juniors,’ and ‘Midgets.’ In some branches there were even ‘Pee Wee’ Vice Lords.
1993		L. Rodríguez Always Running (1996) 52: Clavo, Wilo [...] and I were the peewees, the youngest set.
1997		G. Sikes 8 Ball Chicks (1998) 201: I was a peewee, then juniors and seniors, and then — boom — you’re there, you ladies.
2001		A. Schulman 23rd Precinct 132: Children as young as ten, called ‘Pee Wees,’ are recruited as lookouts [for street dug markets].
2015		P. Beatty Sellout (2016) 63: A click of peewees, fresh out of cholo school.

7. (US campus) a socially insecure young man.

1999

Eble Campus Sl. Apr. 6: pee wee – male who spends much of his time working out and trying to conform: ‘Check out pee wee over there trying to be cool’.