Green’s Dictionary of Slang

1. (orig. US) bizarre, strange, disturbing (fig. approximating the sensation of taking a hallucinogen).

1972		Eble Campus Sl. Oct. 6: trippy – producing effects similar to those caused by drugs.
1975		Harper’s Mag. June 9: In my trippy daze, dope was the filter for the movie camera in my mind, the regulator of my psychic jets.
1989		(con. 1960s) M. Kingston Tripmaster Monkey 242: Hey, man, you want to see something trippy?
1993		D. Jarman diary 22 Apr. Smiling in Slow Motion (2000) 335: I wobbled back to Dickie’s with my trippy eyes.
1999		J. Poller Reach 12: She did these mad swirly drawings – all pinks an’ purples an’ blues. They were dead trippy.
2000		N. Griffiths Grits 16: Acid’s legacy is to make thuh pot a bit more trippy.
2007		L. Redhead Cherry Pie [ebook] ‘Remember the—am I just out of it or was that a really trippy thing to say?’.
2012		J. Fagan Panopticon (2013) 236: The social worker was all like [...] everyone else sees the small cat, but a schizophrenic looks, and they see a lion. ‘Trippy shit’ .
2014		Baltimore Sun (MD) 16 Apr. T26/4: [G]et on cloudy, ambient journeyman Ricky Eats Acid’s even trippier level.
2017		hubpages.com ‘Roadman Slang 4 Jun. 🌐 Trippy - when something is crazy and hard to understand, e.g. ‘it's trippy, one second she hates me and the next she's claiming I'm her only close friend’.

2. (drugs) characteristic of an LSD-taking hippie n.² (3)

1968		Frank Zappa ‘Who Needs the Peace Corps?’ 🎵 I’m hippy and I’m trippy.
1972		Eble Campus Sl. Oct. 6: He’s a really trippy fellow.
1986		J. Ellroy Silent Terror 21: [M]y classmates, a number of whom thought I was ‘cool,’ ‘trippy’ and ‘avant-garde’.
1995		J. Stahl Permanent Midnight 102: Two trippy guys named Maurice and Beppo.
2011		Observer New Review 31/5: This folky, trippy Californian song.

3. (US teen) excellent, first-rate.

1997		L. Davies Candy 5: Fuck, it was nice, in a trippy, gymnastic kind of way.
2013		T. Dorsey Riptide Ultra-Glide 278: ‘It’s trippy watching you waste dudes’.

4. (drugs) pertaining to MDMA.

1997		N. Barlay Curvy Lovebox 186: Regular trippy smiley posse types.
2015		L. McInerney Glorious Heresies 325: Phelan’s words [...] crept up on him like a trippy pill.