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BLOBERT

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Do not laugh but I've found Super Mario Bros very trippy since my first play.
Earthbound is an obvious choise as well but this one below is far beyond anything else:

 

:Flash:

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Vangers: One for the Road
The ultimate level of Russian 90's trippyness put into one game.
 
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unfairlight

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I'm kinda impressed no one has mentioned LSD: Dream Emulator. It's not a very good game per se, but I think it's something that's still worth experiencing. It's procedurally generated and pretty fucking weird.



Reminds me of a bug in Deus Ex: Manass Divided where everything looks fucked up if you alttab.
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I think Hotline Miami is very trippy. It definitely felt like a trip to me while playing - the soundtrack and gameplay definitely work to get you in 'the zone', so to speak.

 

Dawkinsfan69

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Asking for a "trippy game" and then expecting a cohesive story or making a judgement that it's pretentious doesn't really make sense, because that's not how trips work.. Trippy games are designed to evoke or amplify the sensation of being on a trip, and I wouldn't really expect any more intellectual depth out of them than "woah dude check out the fractals man" or something along those lines.

Maybe watch Enter the Void or Requiem for a Dream but those can be tough to slog through idk



That said, recommendations:

Yume Nikki



Hylics


Rememoried


Ilamentia


I think people mentioned earlier, but horror games can have a really trippy feel.. The games by Frictional Games are really good at this (Penumbra Black Plague, SOMA, Amnesia).. LSD's a good one too
 

Cael

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That looks a lot like a Morrowind remaster, actually :D There are some pretty nifty scenery in Morrowind.
 

doolydeath1

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This is gonna be a trip when it's out.
 
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