At My WIT’s End!

21 | ENTP 7w8 | I am the Whole Damn Circus. | @Leonsartstuff on Twitter!

[fandomscreenshots]

Photoshop edit by me.

“Outside of circus hours, the clown could be found cheerfully handing out balloons in town and did not stop until they were all gone.”

This one had been laying around for a while, but due to some personal problems I lost motivation to work on it. Thought it would be a nice opportunity to finally finish it on Bill's birthday!! 🥹🎂🎈

[registeredsinnertm]

They're drunk and in love, your honor

@leocappuccino

[leocappuccino]

Sometimes he’s just tired

[leocappuccino]

A little piece I wrote about some things I’m going through. The symbolism is elegiac in nature. Though, interpretations are always welcome.

[leocappuccino]

Small doodle. I wonder what he’s thinking about.

[leocappuccino]

A Wild Dummy Approaches!  Are you a timey wimey timeline skipping clown too? : 3 

[leocappuccino]

Wit pauses for a moment, staring down at the frantic little wild Dummy perhaps for a moment longer than he ought to.

“…Well. You’re certainly enthusiastic.” He mumbles, a faint smile tugging at the corners of his painted lips.

He waves back at Dummy with a gentle flick of his wrist before leaning his weight onto his cane, the crystalline eye of the raven head glinting an envy green for a split second before returning to its usual cerulean hue.

“I don’t skip through time, dear. I merely experience it differently to those who live through time linearly. Back in my home dimension, time didn’t matter. We had all of time, and yet we had none. Clocks and calendars had no place there, I’ll tell you that…”

The Ringleader clicks his tongue against the roof of his mouth, and a distant expression washes over his features, but the smile returns, and unless one had a keen eye, they’d have missed the brief falter.

“…As for being eternal, I’ve outlived every audience I’ve ever performed for. I’ve seen empires rise and fall…”

Wit grins, an uncanny smile, all fangs and charm.

“I’m still here!” He exclaims emphatically with an exaggerated bow.

“Whether that makes me eternal, or incredibly hard to get rid of is entirely up to you.”

[leocappuccino]

A Wild Dummy Approaches!  Are you a timey wimey timeline skipping clown too? : 3 

[leocappuccino]

Mr. Wittaker here to steal your SANITY.

My pretty boy

[leocappuccino]

Some of the art Wittaker has another person in it does that mean Wittaker has friends besides Pennyyyy? o^O

Mr. Wit gives the question a thoughtful hum, tapping the end of his raven-head cane into the ground rhythmically as if counting the seconds that go by.

“Friends? What a dreadfully… human word.”

He smiles, and whether it’s genuine or mocking is impossible to tell.

“No, no, dear Anon. No friends here. Just me, and my wonderful little circus troupe. I much prefer undying, unquestioning loyalty to trivial, peculiar notions like friendship.”

- 🐦‍⬛🎪

**OOC: He’s very proud of the dedicated staff he’s acquired, that may or may not be… doll-like husks of former victims who do only as he commands. Friendship though? No, no. ☕️**

[the-it-ology-blog]

Imagine we're arguing and suddenly I throw a carnivorous cosmic clown at you.

[leocappuccino]

Hey Wit, do you live in the sewer, is Penny your roomie? O.O

Mr. Wit stares at Anon for a moment, and the silence is almost deafening as he attempts to fathom sharing a space with that smelly creature.

“Ha-ha. I’d sooner stick my head in a box of sand and suffocate.” Says the ringleader, still vividly mentally experiencing living with Pennywise.

He shudders, then recoils and scrunches his painted nose as if he had launched himself face first into the sewers.

“No, no, dear. I reside in my tent. At my circus. Sewers and humans carry the same stench,” He pauses for a brief moment, narrowing his eyes as if to enunciate. “…Shit.”

He waves Anon off with a huff. “It’s enough to share a planet with that overgrown toddler, let alone a sewer.”

[leocappuccino]

Dummy clown going to give Mr Witt clown a big ol' hug <3

Wit visibly reacting to affection:

[leocappuccino]

i need penny and mr. whitt's help bc i'm too c0rny lolll 💀

Pennywise would probably sniff you and think you’re ample opportunity for dinner, and Mr. Wit would exploit you until you’re questioning reality for his own entertainment. Why, pray tell, do you need help? :D

[leocappuccino]

what does wittaker do to capture victims

Wit taps his chin in an exaggerated effort to appear as if he’s pondering his answer. He isn’t. Really, he’s just dragging this on for as long as he possibly can. When he speaks, his voice carries a curious, almost playful sarcasm.

“Capture? An ugly word. Heavens, no.” He leans forward slightly toward Anon, wearing a grin consisting of sharp, dagger like teeth that become impossible to ignore with the proximity.

“That implies effort I simply don’t need to make. I provide people with what they’re looking for and they walk in of their own accord. Humans are wonderfully foolish that way, you see.”

The ringleader waves a dismissive hand and hums softly to himself as though the conversation has begun to bore him.

“By the time they realise something is terribly wrong, they’ve already built the cage for themselves… and driven themselves delightfully mad while they’re at it. I’ve heard humans call this manipulation, but I prefer the term… customer service.”

- 🐦‍⬛🎪

[leocappuccino]

Would Mister Wit also give me a kiss?

Mr. Wit squints and leans down at the stupid anon. “Will Mr. Wit give you a kiss? Will Mr. Wit pay taxes? Who knows! Some mysteries were never meant to be solved.” He stands again, to his full height, and taps anon on the head slightly with his cane. “Truthfully, I’d rather eat a lightbulb. I don’t know what germs you carry. Though, the audacity to ask me that was certainly entertaining.”

- 🐦‍⬛🎪

[minisculemars]

@pennyweek2026 - awaken

it's not that he's TRYING to get clean I just like the idea of him coming out of his 27 year hibernation and swimming out the sewers the first time and unintentionally washing the filth from the last cycle to bring in some new cycle filth :> also doggie paddling because it's funny

[neg4tivecre3p]

My memory is so ass genuinely

hii two little studies anddd some more sketches why not

I have so many more bs laying around but I'm not a fan of how my sketches look rn exactly

anyways