#cuphead self insert

[rexscanonwife]

I finally got around to sketching some ideas for a Cuphead self insert, but I've come to sort of a dilemma! My idea is that she's a savvy business type who likes to do things HER way (and will get quite upset if things are done differently) who works on Roll the Dice basically making sure everything runs smoothly. She arranges the schedule, the light and sound equipment, the band, honestly none of it would happen without her! And all King Dice has to do is SHOW UP and be charming and suave and whatnot 🙄🙄 he gets all the fame and recognition for basically nothing while she stays in the sidelines and kinda resents him for it and also maybe thinks he's cute what

Oh and also! She's secretly a high-ranking demon who works for the Devil 😊 I couldn't decide if I wanted her to be a sheep, as in a wolf in sheep's clothing, or an apple, like the apple that tempted Adam and Eve! So I'm leaving it to you all!

[bobabee-sships]

But your honor.... .. . . Sugar and spice lesbians..... I rest my case

[apocalypse360]

ehrmmm ye drawing Cuphead OC stuff again maybe

[memento-morii-ua]

Drew myself and my OC Morii as a cup-person-

[screwzara]

I'm making a cuphead Self Insert oc :)))))

[carnivalshipping]

Watched s3 a few nights ago and it made me want to redo my Cuphead sona a little more , can a woman not be both a carnival prize And a ventriloquist dummy ? Don’t worry about the logistics there .

[circleheadd]

I've already uploaded this to TikTok and Twitter just because those sites don't really allow for much pomp and circumstance... But last week I put together this Tatty x Cagney (kind of lol) animatic to the tune of "No Girl's Toy" from Raggedy Ann and Andy's Musical Adventure. There's a lot of flirtatious language in the song that, within the context of these two, worked really well, so even though this is ultimately Cagney telling Tatty to get lost, it was a lot of fun to bring that romantic tension to the boards as well... Idk, it's just cute and cheeky and doncha just hate the guy but... darn... Anyway, it would mean a lot if you took the time to watch, because I worked very hard to put this together! Enjoy!

[popfizzles]

Does Boba have any family…?

I conceptualized a younger sibling for Boba once upon a time, but I never really stuck with her. I called her Taro T. as a placeholder name :)

I think they'd be a very "weird little girl (affectionate)" type character, taking over their older sibling's habits of dressing dark and listening to loud music. The type that wears pants until they're tattered, sits alone at lunch, carries a sketchbook wherever they go. I think she'd be middle school age (about 11-15) but tall for their age. Taro would be a reflection of what Boba looked and acted like at that age!

As for who Boba's parents would be, they don't really exist?? The closest I've ever come to designing parents for Boba would be having him speak to a disembodied voice over a phone.

But that's okay! Sometimes cartoon characters don't have parents. :)

[the-evil-lovable-simp]

Fuck….

[kyomaakuma7]

More self inserts please! :)

*holds up $50 for the self insert*

I think you guys would really like this one. My birthday is actually November 8th so this was from a WHILLLEEE ago. But I still love it all the same. Maybe I should redraw it?

The origin of this image? A fanfic. What fanfic you might be asking? …

Anyways! *slowly grabs money* ThaNk yOuuu XD!!

[friendlyfatbee]

Thank y'all for not only being 100 of you for following me, but for 5,000 likes as well! This is insane as this upcoming autumn would mean the second year I've been on tumblr. While it's been a wild ride among my hyperfixations jumping from one franchise to another, I wanted to honor the primarily reasons for your guys' interactions with my little blog: c h a r a c t e r s. Thanks for sticking around so far, and hopefully more wacky moments will commence with the upcoming months!

[fictionalsillies]

Classy ! 💕

I was curious to see what my s/i Crème would look like wearing something other than her usual dress , so of course I picked a suit … I still really like suits :,)👍

I’m also always happy to draw my ladies being happy together , Baroness Von Bon Bon deserves the world ❣️

Hope this little drawing turned out okay !

[love-minor-poltergeist]

Can I please request the Devil from Cuphead with a Lilith s/o? Where they were an early version of Eve that knew Devil before his fall and also fell with him. They too went through a transformation, one that made them insecure as Devil is with his own transformation.

A/N: This was an interesting request! The story of Lilith has always fascinated me. Not to mention that, like the Devil, the numerous pieces of art that were inspired by her tale are absolutely gorgeous! If you haven’t seen it, I’d recommend giving John Collier’s Lilith a look-see!!

I believe I accidentally misread some of the initial request, so the reader falls/transforms before the Devil does. This batch is a little bit heftier than my usual work, so if you’re unhappy with the results, feel free to shoot me a dm so I can make any adjustments where needed!!

┍━━━━━♥♠♣♦━━━━━┑

The Devil with Lilith!S/O:

The Devil’s earliest memories of you traced back to when you were nothing more than a whispered name. Long ago, when he still held a place in his father’s heart, the Devil had watched your conception. 

Even now, the Devil could recall his father’s mumbling under his breath,  enraptured in a conversation of one. The few times the Devil (well, he was Lucifer back then) passed by his office, he could faintly make out his father’s muffled muttering through the door. Most of which were near unintelligible. Save for two names: Adam and Lilith.

After his older brothers’ incessant pestering, the Devil snuck into his father’s office. Crumpled paper balls, broken sticks of charcoal, and empty ink wells littered the floor; the Holy One’s once pristine office left neglected in its master’s fitful working.  

A few steps in, his foot suddenly slid forward. Paper ripped beneath his dress shoe with a loud shriek, startling the angel. Cursing, he lifted his foot up. Beneath him laid two torn halves of a sketch page. A man– broad, curly-haired, and with eyes like a dairy cow– stared up at him; the imprint of the Devil’s shoe marring his otherwise perfect face. 

On the other half was another figure. Sharp, piercing eyes and long hair that flowed  like a waterfall. Ah, so you must be Lilith. It was fascination at first sight. Gingerly, he had picked up the half that housed your striking visage. Without another word, the Devil pocketed it. 

He didn’t know what possessed him to take it. Instinct? Possessiveness? Even now, long after he fell from Heaven, he’s unsure. All the Devil knew was that he wanted to stare and marvel at you for hours on end.

God found out about his son’s trespassing not long after the incident. However, he couldn’t find it within him to be angry towards his favorite son. Instead, he had nurtured the young man’s curiosity. Not that Lucifer ever retained any of his father’s impassioned ramblings. He was much more interested in you. 

“They are to be Adam’s wife,” his father explained, a smile present on his ancient face. A pang ripped through the Devil’s chest. Though he couldn’t quite place why.

By the time his father finally began to sculpt you and your husband to be, the Devil thought whatever torch he carried would fizzle out.  

It did not. 

From the moment you opened your eyes, he had been ensnared. Shyness shook his normally so confident core. And to think that all it took was a gentle tilt of your head and a wry smile. A mirthful glint shone in your eyes as the Devil fought to hide the blush steadily overtaking his face. 

The Devil avoided you like the plague after your birth. He threw himself into his work– hoping that having you out of sight would put an end to this nonsense. Little did he know that absence only made the heart grow fonder. 

He was forced to sit back and observe the object of his obsession from afar– lest he’d make a blithering fool of himself. You were different from most of his father’s pet projects. Disinterested. Both in the role you were given and your husband. 

You always seemed to stare off into the distance. Towards the horizon. Paying the lush paradise and your husband no mind. Hell, you’d even looked annoyed when the only other human around spoke to you. 

The Devil didn’t recognize it then, but you, too, hungered for more; more than what you have, for beyond the garden grounds. Most of all, neither of you wished to be subservient to anyone. 

No matter how much he had tried, you never were able to bond or love Adam like God wanted to. What started out as courteous neutrality steadily gave way into contempt. Resentment bubbled beneath your stony exterior like magma within the earth. You were a ticking time bomb rigged to explode, and the Devil watched on with bated breath.

One day, you snapped. Neither you or the Devil could remember what started the argument. Only that it was enough for you to lash out and claw at your husband’s cheek– your eyes wide and teeth bared like a feral hellcat. Adam was quick to crumple to the ground, hissing in pain. You darted off into the underbrush, the rustles of disturbed foliage and the snaps of breaking twigs following in your wake.

By the time God had found out of your transgressions, you were long gone. No one could find where you ran off to. And though the Devil and his brothers were told to leave the incident behind, one look at his father’s face was enough to say it all: the deity was absolutely livid.

Hours turn into days, days into weeks. Time becomes a blur. Adam gains a new wife, and all is well in the garden once more. The bond between father and son weakens with each passing day; all the while your feral visage burned itself into the Devil’s mind. 

Then that fateful rebellion happened. A sword– burning like the rage within his former brother’s eyes– is pressed to the Devil’s neck; a clear victor had been declared. 

Shortly after, he fell. Screaming and burning until he was only a vague resemblance of his former self.

Life after falling wasn’t easy. He was alone, stripped of any power or influence,  and the phantom pains had haunted him constantly. His wings were broken and useless, forcing him to wander the hellscape by foot, and his appearance— oh, how he had changed. 

Truly, the Devil had hit rock bottom. 

And then, you came back into his life. 

In the centuries– eons– of his existence,  the Devil finds himself at a loss of words around you. You’d regarded him with a level of distrust at first– especially since he had accidentally let it slip that he’s known of your existence before you rebelled. 

It also didn’t help that, in spite of the fall scarring you– having charred the flesh of your arms and legs to a blackened and cracked state; feathers, dark and oil-slick like a raven, grew in uneven patches around your eyes, arms and thighs; and legs twisted and bent until they resembled the hind legs of a goat, complete with hooves – he thought you were absolutely gorgeous. 

It takes a long time for you to trust him. Especially since the last thing you had wanted was to bow down to Heaven’s disgraced golden child.  The two of you shared an acquaintanceship for a while– your interactions kept brief. However, you couldn’t deny that you were a little curious about the man. 

Soon enough, a working business relationship blooms between the two of you. The Devil comes to you in search of information– be it the whereabouts of potential contracts or certain souls on his list. In return, you gain a favor from the soon-to-be King of Hell; you saw how quickly he’s amassing power, you’d be a fool to pass up having someone as influential as him underneath your thumb. 

Not to mention that you may or may not have begun to enjoy spending time with him. What was once small shared rants on how much Heaven sucked ended up developing into something more. 

Once the Devil finally establishes his casino in Inkwell Hell, you find yourself treated as a guest of honor. You’ll be treated better than royalty within velvet-lined walls, an entourage of imps tending to your every whim, and drinks and food are given to you free of charge. Not to mention you have free reign to enter his office or balcony seat whenever you please. 

Acquaintanceship blossoms into an easy, flirtatious.. Whatever you two are. The Devil isn’t sure what to name the relationship he has with you at this point. You both share the same dry, sardonic sense of humor and are content to co-exist in comfortable silence – a part of him rather not muddy one of the few good things he has because he decided to think with his other head, so to speak. 

Then again, there are certain moments where he wonders..

You’d light the end of your thin cigarette against the plump tip of his cigar, eyes hooded and lips pursed as you hummed a low thanks; occasionally glancing at him from the corner of your eye. Chuckling to yourself every time he flushes and grumbles to himself. 

Every now and then you’ll indulge in drinks within his personal office. Occasionally you’d partake of his own cup, gently pressing your lips where his own rested not too long ago. Taking care to slowly lick at your lower lip each time you catch him staring. 

The way you’d pause whenever the larger demon would casually brush  a stray head feather back into place, gently dragging a claw against the vane in his own version of grooming. A shy flush overtaking your cheeks, turning away and covering your mouth as you grumble out to warn you next time.. 

How your gaze softens and body melts when either one of you recall the fall from grace; lamenting former glories and how your transformation left its scars, offering a saddened smile whenever he scoffs at the very idea that your were any less beautiful. 

For as long as both of you existed, for as much as both of you constantly blur the lines of platonic comradery and something the Devil dare not name in fear of getting his hopes up– the two of you are painfully oblivious.

┕━━━━━♥♠♣♦━━━━━┙

[apocalypse360]

@eezy-peezy-charli-squeezy cuphead and mugman HC refs ^^ i may have also made one for mu cuphead oc too.... i wanted the eyes to have color symbolism between these 3 since theyre siblings so yippieee

[electro-bunkit]

lol self insert for BATIM/BATDR & Cuphead

[lazy-b1rdy]

Rewind to 2 years ago when on roblox I drew King Dice from cuphead and someone came up to me in game and started to question/criticize everything about my drawing (art style, the character etc) to the point that i left the game, logged off of my account, and months later almost forgetting my main acc password

THIS PART OF ME HAS BEEN HAUNTING ME EVER SINCE AND I JUST NEEDED TO SCREAM IT OUT BC AT THE SAME TIME IT'S SO FUNNY TO ME

.The drawing is under the cut

pls spare me this was made with a pc mouse when i was like 12-13 idk what was going through my mind at the time T-T

(It makes me cringe so bad bc of the incident now)