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I think I read this as an ebook about 5-6 years ago. The protagonist is the designer of a tabletop role-playing game like D&D. At the beginning of the book, he runs into a crazed fan who pulls out a gun and shoots him in the chest, I think over some perceived slight in how the game system works, and then does something (involving a magic die?) that transports the designer into his game world, where he's forced (I forget exactly how) to be an NPC for the heroic party, who are your usual set of munchkins. There was a female magic-user (who might have been played by a guy) and a male fighter who was ridiculously combat-optimized but lousy at everything else, and later (maybe the second book?) there was an aquatic elf with a spear (trident?) that he shouldn't have at that level where the protagonist realized early on that the character had been built to capitalize on one specific tactic (which comes up near the end of the book where, in a single action, the elf slays dozens of foes). He tries to communicate with them, but the DM decides what his players hear, of course. When the players step away from the game, or engage in an action that takes a long time in-game, but a short time out-of-game (like saying that they're going to march the 20 miles to the castle), their characters kind of go on autopilot, and I think eventually the main character gets the magic-user to develop her own personality, and he gradually falls in love with her.

The primary villain in the game is a masked (helmeted?) Evil Overlord type who wields a terrible magical artifact that lets him completely wipe people off of the face of the Earth (which turns out to be an eraser from the real world). He was masked in part because his face was so beautiful that no one around him could function if they could see it. I think there's a plot point that he has his brother (identical twin?) locked in the dungeons (obviously for the sake of the players, who can free said brother and establish him as the rightful ruler), and as the book progresses, he begins to realize what a bad idea this was tactically (he's beginning to become a sentient character) and I think he has that brother executed. Somewhere near the end of the book, the girl the protagonist has fallen in love with gets sexually assaulted by the warrior character and the protagonist is forced to kill him (the player shows up at the next session with an identical character who is the warrior's "brother" and I think doesn't even bother changing the name). At some point, the protagonist finds a pencil which lets him create things (although the lead is limited, so he can only use it so many times, and he has to try to use it when the DM isn't "looking" at him).

I vaguely recall that the second book in the series involved a Les Miserables pastiche, complete with building barricades in the street, and characters clearly based on the characters of that book, part of a general theme that the guy running the game was very unoriginal. It might have also had a scene where an antagonist operated some sort of well of magic (over a volcano?) and his mother came to visit. She has life-draining powers, and keeps cats, which leads to some description of her holding a cat in her arms with it yowling, trying to get away, as every stroke of her hand pulls life from it. I think the primary antagonist in this one was named The Weatherman due to having control over, well, the weather, which he has due to possessing a real-world item, which I think was either a weather report from the newspaper or a calculator. There was also a plotline about the love interest still experiencing PTSD over the assault and the protagonist finding himself tempted to use the pencil or eraser artifacts to "fix" her, which I think might have led to the location with the magic well as it was where he thought he could destroy them. The second book might have had the players at a convention. I think there was a mention of one of the players not being able to show up because they were exhausted from an all-nighter.

Somewhere in the books, maybe in the first one, there was a scene where I think he was fighting someone (the warrior?) in a set of caves, and he takes advantage of game mechanics by throwing himself off of a ledge, knowing that the falling damage can't be enough to kill him.

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Is this the Death by Cliché series by Bob Defendi...? There are three books in the series, with the first having been published in 2008, and the last in 2018.

Here's the Goodreads synopsis for the first book, Death by Cliché (2008):

To Sartre, Hell was other people. To the game designer, Hell is the game. Damico writes games for a living. When called in to rescue a local roleplaying game demo, Damico is shot in the head by a loony fan. He awakens in a game. A game full of hackney’s tropes and clichéd plots. A game he was there to save, run by the man who murdered him just moments ago. A game that has just become world-swap fantasy. Damico, to his horror, has become the heart of the cliché. Set on their quest in a scene that would make Ed Wood blush, Damico discovers a new wrinkle. As a game designer, he is a creative force in this broken place. His presence touches the two-dimensional inhabitants. First a peasant, then a barmaid, then his character’s own father…all come alive. But the central question remains. Can Damico escape, or is he trapped in this nightmare? Forever. Wait, what? This is a comedy? Ignore all that. Death by Cliché is a heartwarming tale of catastrophic brain damage. Share it with someone you love. Or like. Or anyone at all. Buy the book. Based on a true story.

This reader review hits on some of the other plot points you mentioned:

Damico, game designer, finds himself trapped in a tabletop RPG scenario, as a non-player character, after he got shot in the head by a loony Dungeon Master. (Which in itself is a bad cliché already, but that may be me being a wee bit sensitive after years trying to debunk myths in my hometown, like "oh you're a gamer, so you must be weird and deranged". Meh.) It's only a game, right? Right. So it doesn't matter if all those cardboard characters—peasants, the Evil Overlord, the buxom tavern wench...—get to die, because they're just ink on paper, or in the head of the game master. Except they're not, not exactly; and conversely, if they are, does it mean that Damico is dead, and nothing more than ink as well?

The synopsis for the second book, Death by Cliché 2: The Wrath of Con (2017), mentions a madman in possession of an artifact that grants him complete control of the weather:

Damico is trapped in a fantasy roleplaying game. Not “trapped at the table” like Thanksgiving dinner after a particularly unpleasant election. Trapped inside. Back in the real world he's probably bleeding to death in the trunk of the game master’s car. On a happier note, he currently rules this improbably-constructed world from the very plush Comfy Chair, which he ordered built to replace the previous overlord’s throne. It’s amazing what a true artist can do with hard wood, soft animals, and relaxation magic. Unfortunately, this world exists to serve a fantasy roleplaying game, and players back in the real world have started rolling dice again. An artifact that grants complete control of the weather has fallen into the hands of a mad man, and Damico must join the adventurers in their quest to face-stab evil in the name of justice. Also, he needs to decide whether to become the Dark God of Destruction, so his schedule is filling up quickly.

And the synopsis for the third book, Death by Cliché 3: Boldfinger (2018), mentions the Eraser, an all-powerful artifact which grants the "ultimate power of annihilation":

Damico made a terrible mistake. You see, he didn’t destroy the Eraser, the all-powerful Artifact that gives him the ultimate power of annihilation. Instead, he kept it, and every morning he wakes up and makes the conscious decision not to become the Dark God of Destruction. Worse, he lied to woman he loves about it. I don’t know how things work in your house, but that’s usually the sort of decision you make as a couple.

Months have passed and she hasn’t forgiven him. She doesn’t trust him. She barely recognizes him. He’s starting to fear she doesn’t love him anymore.

And the natives are restless. From the head of his Empire on the Comfy Throne™, he can see the High Lords plotting against him. They urge him to reinstate the tyrannies of the past. They insist that allowing kingdoms to secede peacefully, it shows weakness, and now rebels have risen against him. He empathizes with their plight, but if he lets them go, the High Lords will use this as an excuse to overthrow him, and if he puts them down, he becomes the monster he dreads.

Also, did we mention his kitten has turned out to be the prophesized Cat of Darkness, and that the High Lords just assassinated his only two allies on the council?

Who would have thought you’d be shot in the head, end up in the worse roleplaying game of all time, and things would go downhill from there?

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    The blurb for the second one mentions a weather control thingie
    – Valorum
    Feb 17 at 17:41
  • 2
    Hah! Thank you. That one was bugging me. I kept thinking that one of the books was named something like "Oldfinger". Apparently, the third book is "Boldfinger". And boy, are those reviews mixed...
    – FuzzyBoots
    Feb 17 at 17:49

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