Green’s Dictionary of Slang

1. to swagger, to saunter.

1964		Larner & Tefferteller Addict in the Street (1966) 124: They would walk in doubles or triples, walking tough, diddleybopping.
1969		H. Rap Brown Die Nigger Die! 97: These young brothers came out there woofing, diddy-bopping and raising hell.
1977		P. Hamill Flesh and Blood (1978) 6: He was diddy-bopping, like some dude on Lenox Avenue.
1978		L.K. Truscott IV Dress Gray (1979) 222: Yew think yew are some kinda hot shit, diddlyboppin’ in here outta high school, big hero.
1978		J. Webb Fields of Fire (1980) 255: Asshole here comes diddy-bopping in from the hospital.
1986		S. King It (1987) 925: When a grownup was dirty-bopping down the street, thinking his grownup thoughts [...] he never noticed kids playing hopscotch.
1990		(con. c.1970) G. Hasford Phantom Blooper 7: Down in the kill zone, the Kid From Brooklyn dittybops through budding gardens of metal planted thick with deadly antipersonnel mines.
2000		P. Beatty Tuff 12: Some, like the young man [...] diddy-bopping against the foot traffic, had surrendered to the streets.
2003		A. Swofford Jarhead 30: You don’t throw the weapon over your shoulder [...] like you used to do before diddying down to the local hot spot for squirrels.
2011		G. Hayward Corruption Officer [ebk] cap. 11: He diddybopping around here still trying to live out his heyday. The nigga damn near fifty and he’s still dying his hair, buying gold chains and rings and shit.

2. (UK Black) to run off.

2015

67 ‘Hookahs’ 🎵 Spin, & spin, spin like a yo-yo, make niggas diddy-bop wearing ten boots.