Bodyguard Crimson and his Boss, Alessio, are in the backseat of their limo after a long day of meetings and mafia shenanigans. Crim states with a smile, ‘Long day, eh, boss?’, to which Alessio responds with a muttered ‘Mm-hmm’ and then dozes off.

Crimson watches his boss fall asleep with a soft look as hearts appear next to him, signifying his feelings towards the other man. Crim notices the hearts, and in a panic, grabs them out of the air and shoves them into his mouth (a metaphor for repressing his feelings).

The movement wakes Alessio, who groggily asks ‘Whaz… (what’s-)?” Crimson’s cover story is that he ate a bug, but in saying so, his true feelings slip out. Crim: ‘N-nothing, sir. Just a…a bug.’ In a pink cloud with hearts: ‘I adore you <3’ Crimson freezes, covering his mouth with his hands. A little skull and crossbones pops up above his head, as he thinks he’s made a major faux pas. But in response, Alessio just responds with a nonchalant, ‘Oh, yeah?’, a small smile creeping onto his face as he does so.

Crimson panics, reaching for the door handle, trying to extricate himself from the situation. Alessio reaches over and grabs him by the back of the shirt. Alessio: Do not throw yourself out a moving vehicle, scemacchiotto. Note: I do not speak Italian. I think I cobbled together a word that means ‘little idiot (affectionate)’

Post #CriminAleWeek2025 prompts, Role Swap and Crush Admittance.

Watch your boss fall asleep
Have a Realization
Panic
Swallow your feelings down
Let them out anyway
PANIC!!1!

#HelluvaBoss #CriminAle #HelluvaBossCrimson #HelluvaBossAlessio #BossAlessioAU

Boss Alessio and his bodyguard Crim in Alessio's bedroom. Alessio is half-dressed, sitting on his bed while pulling on his sock. His other leg is truncated at mid-thigh with old bite-mark scars at the end. Crim is walking over to him with an intricate, golden prosthetic leg in his hands.

Morning rituals.

From my Boss Alessio AU - Alessio lost his leg when he was a young mafia don in a serious conflict with a shark demon lover.

#HelluvaBossCrimson #HelluvaBossAlessio
#CriminAle #BossAlessioAU #HelluvaBossFanart

Boss Alessio and his bodyguard Crim are sitting at a picnic table somewhere in the Greed Ring. The two are scheming and Crimson has partway climbed up on the table in his enthusiasm, looking offscreen. There is an alligator-like creature hiding beneath the bushes.

Human designs of boss Alessio and his bodyguard Crim are sitting at a picnic table somewhere in Florida. Crimson is a grungy white man, casually dressed with a Hawaiian floral shirt (with sharks, of course). His hair is wild and spiked similar to his horns. He has a fanny pack stuffed with his throwing knives, some poking through the fabric. Alessio is a black man dressed in a linen suit in shades of blue with gold jewelry. The two are scheming and Crimson has partway climbed up on the table in his enthusiasm, looking offscreen. There is an alligator hiding beneath the bushes.

Up to no good.

More Boss Alessio AU nonsense. The second picture is their human designs. They're scheming somewhere in Florida.

#HelluvaBossCrimson #HelluvaBossAlessio
#CriminAle #BossAlessioAU #HelluvaBossFanart

Alessio as a stoney-faced boss, dressed in expensive clothing and accessories, along with a cane, stands next to the bodyguard Crim, who has a bit of a deranged look as he twirls a throwing knife in the air.

Boss Alessio and bodyguard Crim in color.

I love these two a lot and would like to eventually do a comic or illustrated story with them.

#HelluvaBossCrimson #HelluvaBossAlessio
#CriminAle #BossAlessioAU #HelluvaBossFanart

A multi-colored bush viper character standing with a 50-cal suppressed sniper rifle. They're somewhat geared up for stealth in the Greed Ring, with a bit of camo and green clothes and gear.

Probably the last capo for my Boss Alessio AU. After ‘Oops’, I knew I had to add a snake character. They’re based off of a bush viper. Did I create them just for the pun ‘Viper Sniper’? (yes)

#HelluvaBossOC #SnakeOC #BossAlessioAU

Three little cookie cutter shark characters. All are dressed sharply; one is carrying a revolver almost almost as big as he is, and the other two are carrying a blood-stained moneybag above their heads.

More Boss Alessio AU characters!
I love these guys, they’re based on cookie-cutter sharks. They’re a friends’ favorite shark species and I had to make them into characters. And yes, they’re about a foot and a half (45 cm) tall :P

#HelluvaBossOC #SharkOC #BossAlessioAU

A strong, zebra shark based woman in a pinstripe suit and skirt. She's wielding a large weapon, a gold anchor with a length of chain.

Grace, another Boss Alessio AU character. The bruiser of the team, she’s based off of a zebra shark.

#HelluvaBossOC #SharkOC #BossAlessioAU

Two sexy nurses, based on nurse sharks. One is healing themed, the other is poison themed. Poison nurse has patchwork skin, which is a piebald condition that is rare in sharks. Healing nurse has a syringe and Poison nurse has a dart gun.

Helloooo nurse (sharks)!
Some OCs for Alessio's mafia in an AU where he's the boss and Crim's his gremlin bodyguard.

#HelluvaBossOC #SharkOC #BossAlessioAU

A fashionable Alessio is the boss in this AU. He's snapping his fingers, unleashing a deranged, enthusiastic, plain-clothed Crimson on the viewer. Dang, what did you do to deserve this? >;}

Crimson as a bodyguard. He's in plainclothes, and has a sleeve of knives strapped to his leg.

'Role Swap' prompt from CriminAleWeek2023, with Alessio as a cool, composed boss & Crimson as a little gremlin of a bodyguard. 2nd pic is a bit of a revision to Crim's outfit.

#HelluvaBossCrimson #HelluvaBossAlessio
#CriminAle #BossAlessioAU #HelluvaBossFanart