- In Taking Root 1.10
:- Sly recounting how he injured the puppeteer.
Sly: "Brick smashed him in the face out of nowhere. Puzzling."
- When Sly says that he's always right, all the other orphans start recounting anecdotes to the contrary For the Lulz.
- In Cat out of the Bag 2.8. Sly repeatedly stating how envious he is of his compatriots getting to act out to terrify the crowd and his obsession with the Shepherd.
- In Lips Sealed 3.6, a concussed Sy is displeased that he is forced to look at Gordon's butt, and begins giggling while thinking of whose butt he would rather be looking at.
- In Lamb to the Slaughter 6.3, Sy tries to prove to Jamie that Mary's not mad at him by asking her if they're okay. She throws a knife at him that hits a foot from his head.
Sylvester: I don’t know what that means!
Mary: We're fine, Sy. Now shush!
- Sylvester's frustration over the people's stupidity in Lamb to the Slaughter 6.04.
One day, we’re going to invent a better brain. Then we’re going to put that superior brain in everyone’s heads, and stupid things like this aren’t going to happen, I thought.
I considered it for a moment, then amended the thought to add, as much.
- Helen describing her birth in Lamb to the Slaughter 6.5:
My first time out of the vat. I was only half as tall as I am now. I opened my eyes and wanted to give someone a hug. They shot me.
- Mary getting along with Catcher in Lamb to the Slaughter 6.06, and fangirling over his tools.
Catcher: You like it?
Mary: When I was being trained, I learned to use and make a garrote on a pole, because I was expected to take down adults, and I can’t always reach the throat. I like this, it’s sort of the same, but it’s so clever! And satisfying when it closes. Like, tch, tch, it’s a solid sound. Do you have a silent one?
Catcher: I do have a silent one, and I do have cords, for when I need my target especially silent, too. When we stop to rest, I can get them out and show you.
Mary: What’s that at your collarbone? The metal thing.
Catcher: It goes into the eye socket. Pinch it like this to open it up, hooks go under the eyelids, prying the eye open, and you release, and the rest sits against the socket.
Mary: Why would you need to pry someone’s eyes open? Well, I mean, I can think of reasons, but why not just have a knife?
Catcher: For psychological effect. To make them watch what I do to their friend. Or I can hold their head still, and let water droplets fall on the open eye. The eyes are the window to the soul. Pry at the eyes, and you can shake the soul.
Mary: That is so… oh wow. The way you said it, even. And that one?
- Catcher admitting that he doesn't even know what one of his tools does and he just thinks it looks cool.
- In Lamb to the Slaughter 6.08, Mary gets critically wounded and is bleeding out on the ground, while Sy and Jamie are forced to defend their group with her throwing knives. They are spectacularly bad at it.
Sy and Jamie throw knives, miss simultaneously.
Mary (voice faint): We’re doomed.
Sy: Don’t need commentary!
Mary: Wasting good knives.
Sy: Shush!
- In Tooth and Nail 7.10
Gordon: You beat Lilian down here
Sy: Lies and slander. Oh, you meant I’m first. Yeah.
- This scene at the start of Tooth and Nail 7.15:
Mauer: (points a gun at Lillian's head) Let’s talk.
Sy: Oh man. I’ve really been looking forward to having a conversation with you.
Mauer and Gordon, in unison: Focus.
Sy: He’s posturing.
Mauer presses the trigger. The bullet strikes a wall near Lillian's head.
Sy: Posturing with good aim.
- In Tooth and Nail 7.15, Mary has just ordered her creator's death and is irritated with the Lambs' concern for her:
Mary: I will stab the next person to ask if I’m okay.
Sy: Are you okay?
Mary draws a knife and moves towards Sy
- In Bleeding Edge 8.10, Sy sees the girl the Lambs are looking for enter the lab with a boy, push him onto some crates, and bite his shoulder, without him putting up a fight.
Sy: It was very possible he was even worse at fighting than I was. I felt a kind of pity and camaraderie for the guy.
- While waiting for Mauer to show up at a lab they're staking out in Bleeding Edge 8.13, the other Lambs finally decide to sort out how Sylvester feels about Mauer by asking if he would be romantically interested if Mauer was his age and a girl, but was still an enemy. Sylvester proceeds to stare into space for a minute as he has an Imagine Spot.
Gordon: You’re actually thinking about it. As if it’s actually a consideration.
- In Counting Sheep 9.10, Sy and Jamie have a discussion with Mauer in his camp. Sylvester's mental monologue makes it pretty clear that the third of the world is British.
Mauer took the kettle, a small jar, and a mug from spaces to his right, putting loose leaf tea into the mug before pouring himself a cup.
I knew a lot of tea drinkers, and the fact that he hadn’t served or even offered us any tea was as good as a cardinal sin. I couldn’t think of a better, more vulgar way to give the two of us the middle finger and say ‘we are not friends, here’.
- In Cut to the Quick 11.1, Sy's reaction to his and Jamie's wanted posters:
Sy: "While possessed of no overly extraordinary physical talents or capabilities, these two adolescent males are experienced killers, talented improvisers, and remain devastatingly intelligent in individual, complimentary ways." Devastatingly intelligent. Devastatingly.
Jamie: Don't look so proud of yourself.
Sy: But I’m devastatingly proud.
- Sy then proceeds to forget the word "devastatingly" and has to ask Jamie to remember it for him whenever he tries to play on how pleased he is with the posters for the rest of the arc.
- It keeps popping up in later arcs as a Brick Joke, such as when Sy is recruiting students for his rebellion:
Female student: I recognize him. From the wanted posters. "Devastatingly intelligent", they called him.
Sylvester: You. I like you!
- In Cut to the Quick 11.3, Sy and Jamie's convoluted scheme to deal with Dog and Catcher, including stink bombs, water traps, grenades, setting guard dogs on them to take advantage of their love for dogs, and, finally, surrendering and offering to catch up over lunch, having bought sandwiches while Dog and Catcher were fending off the guard dogs.
Catcher: I don’t trust you.
Sy: It’s fresh. Didn’t even have a chance to poison it.
Catcher: The poison wouldn’t affect me much more than it affects you. Alright, I need to dry off. But you’re going to be good, hear?
Sy: Good as gold.
- From the same chapter:
Sy: He's being hurt right now, damn it! Every second he spends there, he's getting exposed!
Bruno: Language.
Sy: Fuck you!
Bruno: That's better.
- This comes shortly after a Gilligan Cut where Jamie and Sylvester end up with literally every single one of Catcher's restraints on them.
- In Cut to the Quick 11.11, Sy has to tie Jamie up to immobilize him while he performs excruciating surgery to remove the Red Tide spores from him and Sy comments that he'd always hoped that Lillian would be the first Lamb he tied up, "for very different reasons". Jamie, who constantly makes jokes about Sy's astonishing naivete on sexual matters is astounded/horrified, and begs Sy to just let him imagine that there is a completely innocent explanation for Sy's comment. Sy's internal thoughts are that he was actually thinking back to the days when he loved nothing more than teasing, provoking, and prodding Lil, and used to think about how much fun it would be to do that when she couldn't fight back. Sy is genuinely mystified as to what possible "adult" purpose there could be behind tying someone up.
- Sylvester's commentary on the mayor's children in Dyed in the Wool 12.6, whose house was recently set on fire.
Sylvester: How do they do that?
Jamie: Do what?
Sy: Those kids. (points) Look at them. Yes, they’ve been running around, and they’re a touch disheveled, but they’re so prim and proper, dressed like they’re ready to go out to dinner, with their shirts ironed and everything matching. Do they just have late bedtimes, or is that how they dress for bed?
Jamie: I think you’re putting too much thought into this, Sy.
Sy: Hair neatly parted for the boys, tidy curls for the girls. The eldest boy is wearing a tie, Jamie. A tie! Our house is on fire. It’s the middle of summer, sweltering, and the city’s going to be even hotter, by the looks of those five other fires we can see out the window. Get on out of bed, sons and daughter, get your shirt on, button it up, put on your tie, we can’t have you looking slovenly. Sit down at the dressers while the nanny does your hair. Don’t mind the smoke or the tongues of flame licking at your feet in the meanwhile.
Pierre: It is a bit strange.
Sy: I mean, I’d expect this from Helen, but this is a well-to-do family in a not-too-important city. Dear nanny, given the immediate circumstances, perhaps we shouldn’t use the flammable oils to slick down Junior’s hair.
Jamie (in a tired voice): Is it really that important?
Sy: Yes!
Jamie: Why?
Sy: Because I want to know!
- In Black Sheep 13.1, Sy's welcome preparations for Duncan, Ashton, and the three honorary Lambs with them: Leaving them pets.
Duncan: *touching base with the other Lambs* A lamb. Because he apparently thinks he's funny.
—-
- Lillian later asks Sy what was with the chicken, and Sy merely says he thought some variety might help. When she mentions that Duncan took the chicken as an insult, Sy slaps his head and goes "I wish I'd done that on purpose!"
- In Black Sheep 13.9, Ashton needs to give the Devil a direct dose for interrogation purposes. He goes to administer them orally, but...
Lacey: Ashton, do not kiss that man. You don't know where he's been.
- In Arc 15's Lamb interlude, Jessie is reminiscing.
Sy: *presiding over a fight between Gordon and several other orphans* For too long, you've made fun of my fighting skills. I challenge you!
Gordon: *is being dogpiled* Not the time!
Gordon: Drop dead, Sylvester! Jamie, help me!
Sy: I'll give you my dessert tonight.
Gordon: Mary!
Sy: Mary, I will tell them about the hearts.
Gordon: Helen, I will buy you cake.
Sy: I'll buy you more cake.
Gordon: Lillian!
Lillian: Why am I the last person you ask?
- In Head over Heels 16.12, Sy and his team are being surrounded by Tender Mercies, who taunt and try to intimidate them. Sy is not impressed.
Tender Mercy: Gonna put my hands under your skin! Reach all the way inside you!
Sy: I used to hang out with someone who talked like that over tea! It’s not that creepy!
- At the end of Head over Heels 16.13 and into the beginning of Gut Feeling 17.1, Sy has been finally caught by the Lambs. Among them are Lillian and Mary, two of his old love interests. And where do they find him? In bed with Jessie and Mabel! Mary's first reaction is to try to shoot him.
- To be fair, Sy did react to seeing them by telling Mabel that Mary just wanted to "go for a ride on the Sylvester train". Mary wasn't to know that he thought they were hallucinations trying to take over his mind.
- Partway through Gut Feeling, we're introduced to Helen's "half-brother", Nephilim One, a giant man who is in the middle of wrecking a city. Naturally, Helen and Sy immediately focus on the fact that he's naked, and start making penis jokes in order to fluster Jessie.
Sy: You're just upset because Helen and I are on the same page, while you're on the other side of the aisle, disparaging her brother's slumbering dragon.
Jessie: [snorts in laughter]
Helen: So rude. It's certainly nothing to laugh about.
Jessie: It's so inefficient! Why even tack it on?
Helen: You have no reason to believe it's inefficient. You haven't seen it in use.
Jessie: [claps her hands over her ears and tries to run away]
[later]
Sy: It was either that, or I was going to gesture something like 'big sleep dragon'.
Jessie: We don't have a gesture for 'dragon'. 'Lizard-beast'?
Sy: [gestures 'Man-Meat']
Jessie: [can't stop herself from giggling]
- It's both funny and heartwarming that even after he basically went insane and lost himself, there was still enough of Sy left that when he was turned into a noble, he had the doctors make him taller than the other nobles.
