Green’s Dictionary of Slang

1. to make a ‘clever’ comment that impresses no one, to pose as more sophisticated than one actually is [cite 1901 prob. a misinterpretation].

1911		Winnipeg Trib. (Manitoba) 9 Dec. 19/1: ‘Crack wise’ — To speak in the language of the crooks, instead of the language of ‘the sucker’.
1925		Gleason & Taber Is Zat So? I ii: Will you crack wise? Dat dame’s got brains.
1931		C.B. Yorke ‘Snowbound’ in Gangster Stories Oct. n.p.: I was all set to crack wise at him.
1934		(con. 1920s) J.T. Farrell Young Manhood in Studs Lonigan (1936) 192: If he cracks wise about it [...] I’ll just tell him all right. [Ibid.] 378: She was worth looking at, and they should be envying him, but let them crack wise or dirty!
1942		W. Pegler George Spelvin Chats 77: Whatever you do, somebody squawks. They crack wise about your wife. Remember how you used to crack wise?
1949		R. Chandler Little Sister 219: This bird hasn’t cracked wise yet.
1959		W. Burroughs Naked Lunch (1968) 82: Some citizen cracks wise about giving it back to the Indians.
1977		C. McFadden Serial 102: I’m not going back to the same old lifestyle with you cracking wise and putting me down.
1981		J. Ellroy Brown’s Requiem 207: I had wanted to crack wise and kick ass on those who deserved it.
1990		S. Morgan Homeboy 20: These weren’t your regular cops, your SFPD cracking wise and goofing with the girls.
2005		J. Stahl I, Fatty 207: It probably wasn’t the wisest move: cracking wise.
2013		T. Robinson Hard Bounce [ebook] One guy got himself throttled by Junior when he made the mistake of cracking wise about our sexual predilections.

2. attrib. use of sense 1.

1969

‘Iceberg Slim’ Pimp 109: Keep those ‘crack-wise’ niggers out of your face.