Green’s Dictionary of Slang

1. nonchalant, unconcerned, in control; also adv (see cite 1928).

1886		Lantern (N.O.) 22 Sept. 2: The brother of a pretty flip reporter on one of our daily contemporaries.
1890		Sporting Times 12 Apr. 7/1: Should any member become ‘too flip,’ he is yanked into a place known as the Solitaire, and fed upon bread and water until he is considered to be in a more amiable state of mind.
1902		Ade Forty Modern Fables 106: The Girls in such a Sub-Center of Civilization are about seven times as Flip as what they have to choose from.
1911		J. Lomax Cowboy Songs 265: His manners they are pleasant / Instead of flip and rude.
1917		Wodehouse ‘Crowned Heads’ Man with Two Left Feet 98: He of Tennessee would then sasshay up in a flip manner.
1922		S. Lewis Babbitt (1974) 105: We’re all so flip and think we’re so smart.
1926		A.C. Inman 17 Oct. diary in Aaron (1985) 320: He is conceited, flip and fresh.
1928		W. Winchell Your Broadway & Mine 5 Dec. [synd. col.] ‘It seems to me,’ she flip remarked to the authors, ‘that with you guys it’s still all work and no Play’.
1931		Irwin Amer. Tramp and Und. Sl. 76: Flip.–Flippant; pert; outspoken. Usually applied to anyone with a great deal of ‘brass,’ ‘nerve,’ ‘gall.’.
a.1946		‘The Open Book’ in G. Logsdon Whorehouse Bells Were Ringing (1995) 116: They’re cocky and flip with the lip, / But they know more of plows than they do about cows.
1958		R. Chandler Playback 36: Another flip, hard-boiled modern cutie.
1964		H.S. Thompson letter 7 Mar. in Proud Highway (1997) 441: I didn’t mean to be flip up there in Tacoma.
1973		D. Goines Street Players 27: You brought most of that down on yourself by your flip answers.
1982		A. Maupin Further Tales of the City (1984) 212: I’ll thank you not to be so flip!
1999		Indep. Rev. 29 July 11: They start out cocksure, cool and flip.
2006		G. Pelecanos Night Gardener 283: I didn’t mean to be flip about it.
2024		D. Swierczynski California Bear 138: The pained expression on Aunt Reese’s face made the Girl Detective regret being so flip.

2. exciting, excitable, eccentric, crazy.

1922		S. Lewis Babbitt (1974) 272: The G.C.L. can finally send a little delegation around to inform folks that get too flip that they got to conform to decent standards and quit shooting off their mouths so free.
1924		G. Henderson Keys to Crookdom 404: Flip. Garrulous.
1930		W. Winchell On Broadway 22 Jan. [synd. col.] To hear the flip crackers argue it the only exercise the New Yorker gets is walking out of the average Broadway show.
1952		(con. 1948) G. Mandel Flee the Angry Strangers 388: You crazy broad. Jeez, you flip broad.
1959		J. Blake letter 23 Sept. in Joint (1972) 145: A sort of hipness that is more flip than hip.
1961		L. Block Diet of Treacle (2008) 96: He liked the type – the face, the whole flip structure.
1977		(con. 1969) M. Herr Dispatches 57: Flip religion, it was so far out you couldn’t blame anybody for believing anything.

3. sexually perverse.

1991

De La Soul ‘Millie Pulled a Pistol on Santa’ 🎵 There’s no way that you can prove to me that Dill’s flip.