Deadly Premonition. It's a cult classic, just a really weird game with shoddy translation and awkward cutscenes that barely make any sense but is somehow still self-aware.
Darkest of Days. You're one of Custer's soldiers at Little Big Horn who gets recruited to be a time cop and travel around the timeline fighting in historical battles with ridiculous futuristic weapons to create "balance" or something.
Think this was a genre of 2000s era flash games. Newgrounds, addicting games, etc.
Recall many that were trash like throwing tomatoes at Brittany spears while she spins on a carnivel wheel, shooting terrorists as Bush in white house (ok that one was fun).
One called ray where it was a violent hit man choose your own adventure type game. Controlled a south park character walked them through cutscnes of them killing people and doing coke.
The original Sven co-op. It’s basically a
Half-life mod that turned the single player game into a multiplayer.
Many times the maps were altered for compatibility and to increase difficulty. Many times the map editors were new to the concept. Whatever the reason, it led to bugs and cheap game design mechanics that are annoying solo but great fun when experienced as a group.
Phantasmagoria fits in the actual B-movie way with its FMVs. Many games from the early late 80's and 90's fit this, actually. Plumbers Wear Ties and pretty much any video games with live action filmed shit, because it was almost all universally poorly acted.
I can't really think of a game thats gameplay is so bad it becomes funny other than the GOAT: Big Rigs Over the Road Racing.
Sonic 06 is the OG of "trashy games you can't look away from because in all the ways it sucks, it is NEVER BORING"
... This is why it had such a powerful reputation-ruining impact, by the way.
If it had been boring bad (like Sonic Blast in the 90s or Sonic Boom a few years later) no one would have cared -- Instead it is such a glorious trainwreck that it is basically The Room of video games.