Green’s Dictionary of Slang

1. (orig. US) an amusing, successful, exciting person.

1969

H. Rap Brown Die Nigger Die! 28: They call me Rap the dicker the ass kicker / The cherry picker the city slicker the titty licker.

2. (US) a shoe or boot, esp. a pointed man’s shoe.

1968–70		in DARE questionaire.
1996		Eble Campus Sl. Mar. 1: ass kickers – boots.

3. (orig. US) an aggressive, domineering person, a bully.

1962		R. Dougherty Commissioner 337: We cooperate and get our heads knocked in by that ass-kicker Joe Caron.
1968		T. Wolfe Electric Kool-Aid Acid Test (1969) 74: If somebody is an ass-kicker, then that’s what he’s going to do on this trip, kick asses.
1979		‘Iceberg Slim’ Airtight Willie and Me 25: Some ass-kicker was a cinch to be a ’ho short when the joints folded in the a.m.
1987		(con. 1967) E. Spencer Welcome to Vietnam (1989) 137: He isn’t a firebreathing asskicker type like me.
1990		(con. c.1970) G. Hasford Phantom Blooper 46: But Marines are not construction workers. [...] We are stone-hard kickers of enemy ass.
2001		N. Green Shooting Dr. Jack (2002) 119: He was an ass kicker.
2013		H. Lessig ‘PIN’ in ThugLit July-Aug. [ebook] [M]enacing drifter, paramilitary ass-kicker or twitchy, socially misfit vigilante.

4. an unpleasant place, a challenging situation.

1976		(con. 1969) C.R. Anderson Grunts 107: This ain’t no hill, Man [...] it’s gonna be a real ass-kicker.
1982		(con. 1970) J.M. Del Vecchio 13th Valley (1983) 165: This place is goina be an asskicker. Look how steep that fucker is.