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[Sappho]

Worst ones I can think of:
Day One: Garry's Incident (currently 2 monies)
Unearthed: Trail of Ibn Battuta (currently 5 monies)
The Witch's Yarn (currently 2.24 euro)

They're all above the requested price range, but still quite cheap, and really, truly, dreadfully awful. So bad I hesitate to even suggest buying them as a gag, lest the monsters who made these games actually make any more money off them. Only ones I can think of that haven't already been mentioned.

[MonkeyHead]

If you can find any games by MDickie for the right price you would have a winner on your hands. They are legendarily bad. Hard Time is a prison simulation with so much wrong with it I don't know where to begin. The You Testament is a Jesus RPG/Sim, and The You Testament 2 is a Mohammed RPG/SIM. All use the engine from a wrestling game, so it is totally feasible for any of the characters to suplex someone at any time.

[lijacote]

Worst ones I can think of:
Day One: Garry's Incident (currently 2 monies)
Unearthed: Trail of Ibn Battuta (currently 5 monies)
The Witch's Yarn (currently 2.24 euro)

They're all above the requested price range, but still quite cheap, and really, truly, dreadfully awful. So bad I hesitate to even suggest buying them as a gag, lest the monsters who made these games actually make any more money off them. Only ones I can think of that haven't already been mentioned.

Yeah. I'd suggest that OP take a free and awful game and pack it up as if it was a premium game. Like I think some people here suggested. It'd be nice.

[Shadowlord]

What about Big Rigs: Over the Road Racing?

(I had actually forgotten its name! To remind myself, I went to Metacritic, sorted all the PC games for all time by score, skipped to the last page, and there it was, the very last game with the very lowest score!)

[MonkeyHead]

What about Big Rigs: Over the Road Racing?

(I had actually forgotten its name! To remind myself, I went to Metacritic, sorted all the PC games for all time by score, skipped to the last page, and there it was, the very last game with the very lowest score!)

Ah, but that game is so bad its good.

[Cowboy Colt]

Good shout on Big Rigs.

[majikero]

Good news is that there is Steam Sales!

That means all those shovelware that had made it into Steam is trying to cash in and going on sale. You should expand your budget to $5.

[Sensei]

If you can find any games by MDickie for the right price you would have a winner on your hands. They are legendarily bad. Hard Time is a prison simulation with so much wrong with it I don't know where to begin. The You Testament is a Jesus RPG/Sim, and The You Testament 2 is a Mohammed RPG/SIM. All use the engine from a wrestling game, so it is totally feasible for any of the characters to suplex someone at any time.

You didn't pay money for those did you? I think those are still free on his site.

...oh god, he started charging for on mobile, didn't he? OHHH GOOOODDD!

[Graknorke]

If you can find any games by MDickie for the right price you would have a winner on your hands. They are legendarily bad. Hard Time is a prison simulation with so much wrong with it I don't know where to begin. The You Testament is a Jesus RPG/Sim, and The You Testament 2 is a Mohammed RPG/SIM. All use the engine from a wrestling game, so it is totally feasible for any of the characters to suplex someone at any time.

Burn the collection onto a CD? That sounds like it might be good.
And MDickie really is a character. I would enjoy listening to him talk, at least for a few minutes. Probably not more because he'd get obnoxious fast.

[Elfeater]

Im getting three of my friends 100% orange juice

[Neonivek]

I'm talking about this Air Control.

OHH my gawd! That guy sounds like a hammy radio show personality. 5 seconds in and I love it!

---

Edit: Nevermind... he gets increasingly annoying...

[Cowboy Colt]

You could grab and then burn an awesome freeware, retro, horror game like Babysitter Bloodbath and put it in a VHS box with a custom cover.

[Neonivek]

Make an RPG maker game.

[Nighthawk]

If I really wanted to annoy someone I would send them this little gem.

[Arbinire]

I'd say Depression Quest, Gone Home, or Stanley Parable.

Then you get the added bonus, if he hates it you can just tell him he's not hip enough and he doesn't understand the *insert pretentious hipster bullshit social justice warrior rant*.  And if he does like them, you can call him a pretiontious hipster bullshit social justice warrior