Green’s Dictionary of Slang

1. annoying, irritating.

c.1930		(ref. to late 19C) N. Kimball Amer. Madam (1981) 107: We saw their nasty little habits, gestures of loneliness, no doubt. My, how blue and dragass a millionaire [...] can be with a twenty dollar whore at two in the morning.
1949		N. Algren Man with the Golden Arm 286: A drag-ass ignoramus. A stooge. A bottom-of-the-heaper.
1978		H. Selby Jr Requiem for a Dream (1987) 170: The drag ass process of being booked.

2. of a person, lazy, bedraggled; thus as n. a lazy person.

1952		E. Hemingway letter 24 Feb. in Baker Sel. Letters (1981) 753: If I start to feel low, tired or drag ass I start them [vitamins] again.
1960		(con. 1940s) D. MacCuish Do Not Go Gentle (1962) 117: The lousiest drag-ass bunch of mother-eatin’ piss-drinkin’ fart sack-lovin’ pack of homos I ever seed.
1984		A. Sample (con. late 1950s-early 1960s) Racehoss 177: ‘Boss, git them Gotdam drag-asses outta the way up thar an let this Number 1 squad cum by’.

3. of a thing or person, tedious.

1976

R. Price Blood Brothers 113: After a drag-ass week [...] Monday came as a total shock.

4. slow-moving.

1975

J. Roe Same Old Grind 103: ‘[H]e’s got to take Millie to the hospital [...] No time for the drag-ass ambulance’.

5. tired.

1987		J. Ciardi Good Words 1229: I’m drag-ass.
1996		Eble Campus Sl. Sept.