Ryan's runs always start with him encountering Ghoul, an extremely dangerous undead cryokinetic psychopath. He even kills Ryan on their first encounter, when Ryan is caught by surprise. Every time after that, Ryan rams him with his car, then cheerfully beats him to a bloody pulp with whatever random weapon he's found.
The first time Ryan joins the Augustie, he is annoyed by the truthteller, Luigi, who makes him spout some embarrassing things. In the loop where he joins with Shroud, he completely forgets that he's actually a mole, and Luigi forces him to confess, at which point Jamie murders him. Eventually, Ryan realizes he can't infiltrate the organization while Luigi is active, and goes after him with a hockey stick and puts him in the hospital. It still took him a while to figure this out.
Jamie: How did the maniac even know where he lived? Ryan:[thinking] Actually, it took him longer to find the hockey stick. It was truly a dying sport.
Ryan is aghast that Sparrow, one of the deadliest members of the Augustie, has a power that has nothing to do with sparrows (she uses lasers).
Sparrow:[defensively] I like sparrows, okay? They're my favorite animal.
Book 2:
Ryan refuses to join Dynamis unless he gets a purple cashmere suit; Edgar refuses, saying it's up to the hero Wardrobe to design all the costumes. Ryan and Wardrobe immediately agree that he definitely needs a cashmere suit, and Wardrobe even convinces him to upgrade to a bowler hat and a scarf.
Atom Cat: Oh god, now there's two of them.
Livia notes that Luigi was hospitalized by some maniac in a hockey mask. Ryan had no intention of being in a situation where he'd encounter Luigi this loop, but he still went out of his way to get rid of him.
When Shroud is bleeding out and Wardrobe can't fix him, the Panda suggests she turn into Jesus and heal him. This is apparently something that's come up before.
Wardrobe: I CAN'T SOLVE EVERYTHING BY COSPLAYING AS JESUS!
After being captured by the Meta Gang and freed by Sarin, the pair encounter Psyshock and Frank the Mad. Ryan... pretends to be a CIA agent, orders Frank to arrest Psyshock for the murder of Adam, and stops time to put a bloody hammer in Psyshock's tentacle to claim he was going to attack Frank from behind ("You're immune to metal! I couldn't hurt you even if I wanted to!"). Eventually, Frank turns on Psyshock, to his exasperation.
Psyshock: You're not even American!
Once the Meta Gang is subdued, the Reptilian demands to know why Ryan is in charge, since he was just recently their prisoner. Ryan puts it to a vote. Frank the Mad, Sarin, the sapient Black elixir, and the dozens of murderous bunnies all raise their hands for him. The other Psychos quietly go along with it.
Ryan: I love democracy.
Livia has her notes from her previous self, but brings along the truthteller Luigi to make sure Ryan is being honest. Ryan takes a little too much pleasure going into full detail.
"I am a time-traveler, and I've been at it for centuries. I've lived a full life in Monaco, which I don't recommend, and I've tried pretty much everything you can think of. Including beating you up, Luigi. Livia, you can make notes that carry through my time jumps, so everything you wrote down is true; this is the third loop where we meet and I really hated how you took away my control over all factors, but like cancer, I've learned to live with it. Also, you really remind me of a friend who suffered from a toxic family environment, so I want to help. I beat the shit out of the Meta-Gang last loop before they could kill everyone with an orbital laser, but your daddy waged war on the Carnival and Dynamis and the city burned again. "I saved your ex-boyfriend from your aunt for you, but she ended up killing Fortuna instead, and your Lightning Dad smashed a Living Sun into New Rome and I had to reload. But Psypsy managed to follow, which didn't end well for him; I helped feed Big Fat Adam to a black alien whom I called Darkling, because it eats hope and happiness. Then I gave the Meta-Gang the democratic choice of voting for me or dying, I became President, and I love democracy so much I'm never relinquishing power until my death. The whole timeline is ruined so I decided to try new stuff like finding a cure for the Psycho condition, and also, you have the brain patterns of a friend trapped in your head, which I really want back, please. I haven't doctored your notes or anything, and I have no intention of causing you trouble until you go after me first. "Except for you Luigi. I hate you, I hate you so much. The first time I beat you was one of my eternal life's best memories, and I love doing it. I love it so much I'll keep doing it in every loop until the last one. Also, nothing you will do during this loop really matters since I'll reload eventually, so your life is meaningless. You don't matter." Ryan joined his hands. "I think that's all." By the time he had finished, Livia's fingers fidgeted around her coffee cup, and her gaze lost itself in the pitch darkness of her beverage. Luigi's stare had turned distant, as he underwent an existential crisis.
Ryan takes over the Dynamis-run news station to release news of Hector's crimes and what's going on with the knock-off elixirs. This includes a puppet show, a ransom demand, and a live nuclear bomb. Which he lets his cat play with.
"They can't silence the truth!" the president went on a rant before the camera. "We shall not give up in the face of intimi—" Bleep. Ryan glanced at Eugène-Henry, the cat having pushed the A-bomb's big button and triggered the countdown. "Well." The president looked back at the camera, and smiled behind his mask. "That's all folks!"
Ryan hams it up even more upon meeting Wardrobe, in particular demonstrating how he tricked her into making the very supervillain costume he's now wearing.
"I designed his costume!" Wardrobe paled in horror at the terrible truth. "But I didn't know someone would use it for evil!" "It has skulls on the socks!" Felix snarled, pointing a finger at Ryan's boots. "What did you expect?" "That's right, Wardrobe," Ryan said, his voice as deep as the darkest abyss. "By creating this cashmere cashmere suit, you sowed the seeds of your own nemesis. A grim darkness born of your shining light." "My... my nemesis?" Emotion broke through Wardrobe's face, as her wish for a flashy supervillain archenemy was granted. "I have a secret nemesis?" "Yes, you do." Ryan extended one hand at her, holding Eugène-Henry with the other. "Join me, Wardrobe. Become my archenemy, every day of the week. Together, nothing can stop our brand. We will build a multi-billion euro franchise, greater than even Star Wars! We will flood the market with merchandise, and we will rule the box-office! Only through me, can you achieve the popularity you crave!" "Yes, yes! Oh Mr. President, I accept your offer!" Wardrobe surrendered to the lure of a long-term exclusive rivalry. "We'll be fighting forever!"
In their last encounter in the loop, Wardrobe is fighting against Ryan despite everything because Dynamis has Nora hostage. So he proposes. It almost works, too.
Wardrobe covered her mouth with her hands in shock at his proposal, while Len abruptly stopped her work to look over her shoulder. The president ignored his childhood friend and focused on his archenemy.
Book 3:
The heroes discover a cure for the Psycho condition: If they can talk to the elixirs and convince them to modify their host based on Livia's unique genetics, then the elixirs will think they're two people in one body and separate. They set up a translator to talk to the elixirs... and it turns out that they're constantly bickering. And they've apparently been at this the entire time.
"The Panda..." The manbear coughed. "The Panda is having a tough family flashback." "Me too," Len said, biting her lower lip. Hanlon's razor. Never attribute to malice, what can be explained by incompetence.
Throughout the series, whenever Ryan confronts Enrique Manada, one of the guards points his laser sight at his crotch. When they go to arrest Doctor Tyrano, the same thing happens.
"Boris, how many times will I have to tell you," Enrique told one of his bodyguards with exasperation. "Not the nuts." "He's keeping a secret weapon there, sir," the guard defended his choice of target, which Ryan found the wisest of them all. "I can feel it in my bones."
