Maestro Psychopomp
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maestropsychopomp.bsky.social
Maestro Psychopomp
@maestropsychopomp.bsky.social
170 followers 38 following 380 posts
36 | Artist + Writer | You'll mostly see Crimson and Alessio when I get the nerve to post
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Reposted by Maestro Psychopomp
tmoe97.bsky.social
Hey all! Just dropped a spicy new collab on AO3, I had the pleasure of working with @ghostyhaunts.bsky.social on this particular piece. Where Crimson's curiosity once again gets him more than he bargained for 🤭
archiveofourown.org/works/76757616
#HelluvaBoss #Criminale #fanfiction
December 31, 2025 at 4:31 AM
Reposted by Maestro Psychopomp
norrynator.bsky.social
Good Dreams 💤

#HelluvaBossCrimson
#HelluvaBossAlessio
#HelluvaBossCriminAle
#CriminAle
Comic of Crimson waking Alessio in his bed reaching for his pillow gun. Crimson craws into Alessio's lap and kisses him before Alessio wakes and realizes it's a dream. Alessio curses and walking ensues. Bonus page for Ko-fi supporters only. NorryArt Bonus image Bonus image
December 27, 2025 at 8:24 PM
Reposted by Maestro Psychopomp
norrynator.bsky.social
Fighting the art block bc I won't let slop win. 😤

#CriminAle
#HelluvaBossCrimson
#HelluvaBossAlessio
#HelluvaBoss
Alessio and Crimson sketches NorryArt
January 4, 2026 at 5:28 AM
Reposted by Maestro Psychopomp
creatoringo.bsky.social
#HelluvaBossFanart
#CriminAle

🔞ではありませんが、おおきなお友だち向けです
January 6, 2026 at 12:17 PM
Reposted by Maestro Psychopomp
creatoringo.bsky.social
いずれ本になる予定のとあるシーンの進捗です💪

#CriminAle
January 2, 2026 at 7:32 PM
Reposted by Maestro Psychopomp
astsa.bsky.social
#HelluvaBossCrimson
#criminAle
#moxxie
クリムゾンの漫画を描きたいんだけどしばらく描けそうに無いから落書きで描き溜め
妄想と幻想が強い
これからプロットは描くのでいつか漫画でちゃんと描けたらいいなぁ❣️
January 2, 2026 at 3:09 AM
Reposted by Maestro Psychopomp
psunnysunq.bsky.social
#HelluvaBoss #HelluvaBossCrimson #HelluvaBossAlessio #Criminales
I specially drew a background panel for the official standee!!
Once it’s attached to the T-shaped acrylic base, it stays very stable.
January 5, 2026 at 5:25 AM
Reposted by Maestro Psychopomp
psunnysunq.bsky.social
#HelluvaBoss #HelluvaBossCrimson
I was happily thinking, “Yeah~ the headscarf and coat have to be dark red ✨”
but then I realized… Crim himself is already red.
Put together, it’s basically just a whole lump of red, hahaha.
January 7, 2026 at 5:13 PM
Reposted by Maestro Psychopomp
indulgentnine.bsky.social
#helluvaboss #helluvabosscrimson #crimson #HelluvaBossFanart
January 7, 2026 at 12:00 AM
Reposted by Maestro Psychopomp
strike-director.bsky.social
PLEASE 🔥 CRIMINALE community we need to manifest this‼️ Seriously, I buy from every merch drop they make at this point. Crimson, Alessio, if they made Stu, I would buy him too!

#helluvaboss
#helluvabosscrimson
#helluvabossalessio
ghostyhaunts.bsky.social Chaz the Party Shark 🎉 @ghostyhaunts.bsky.social · 1d
Oh yay, my pre-order Halloween 🦈 🤖 stuff is finally shipping soon! 🤩

I’m so pleased with how many drops Crimson, Alessio and Wally were included in last year. (Chaz and Striker too, of course!)
I hope the momentum continues for the inevitable Valentine’s Day drop next month 👀
January 7, 2026 at 1:37 AM
Reposted by Maestro Psychopomp
norrynator.bsky.social
My hand slipped and the Old man Yaoi went toxic ☺️🔪

#HelluvaBoss
#HelluvaBossCrimson
#HelluvaBossAlessio
Crimson holding a knife to Alessio’s throat. NorryArt
December 19, 2024 at 7:20 PM
Reposted by Maestro Psychopomp
twocoffeedraws.bsky.social
Wanted to draw something fun, so here's the boys on vacation :3

#HelluvaBoss #CriminAle #HelluvaBossCrimson #HelluvaBossAlessio
Crimson and Alessio on a motorbike in Italy, on a road overlooking the ocean and coast. Crimson looks a bit manic as he pops a wheelie and goes way too fast. Alessio is catching his hat before it flies off and looks mildly distraught, perhaps for more than one reason ;3
November 13, 2025 at 8:06 AM
Reposted by Maestro Psychopomp
twocoffeedraws.bsky.social
A little softness.

#HelluvaBoss #CriminAle #HelluvaBossCrimson #HelluvaBossAlessio
Alessio and Crimson in the back of a limo. Crimson has nodded off and is leaning against Alessio as he naps. Alessio has a soft look as he gazes down at his boss. His jacket is draped over Crimson and their tails are overlapping.
December 21, 2025 at 10:53 PM
Reposted by Maestro Psychopomp
psunnysunq.bsky.social
#HelluvaBoss #HelluvaBossCrimson #HelluvaBossAlessio #Criminales
It’s a tough choice.😩

(I’ve put the related links in the comments.)
December 23, 2025 at 6:29 PM
Reposted by Maestro Psychopomp
psunnysunq.bsky.social
#HelluvaBoss #HelluvaBossCrimson #HelluvaBossAlessio #Criminales
"I told you to unwrap it, not rewrap it!!!!!"
December 25, 2025 at 6:55 PM
Reposted by Maestro Psychopomp
psunnysunq.bsky.social
#HelluvaBossCrimson #HelluvaBossAlessio #Criminales
2026 Happy New Year~~
December 31, 2025 at 7:32 PM
maestropsychopomp.bsky.social
I drew this to go with a CriminAle fanfic I'm writing!

Alessio sends an annoymous message to Crimson. I hope it goes well! 📱💌

archiveofourown.org/works/760281...
Crimson is at his desk, looking at a phone that has just received a message. He's surrounded by the silhouettes of some of his Mafia crew. Alessio is in the foreground, holding a glowing phone that he's prepped to put away into his coat. He's looking over his shoulder at Crimson with a worried expression.
December 19, 2025 at 6:00 PM
Reposted by Maestro Psychopomp
ghostyhaunts.bsky.social
😈 CriminAle 🦈

My titles are unmatched, I know.
Anyway, noooot been having the best time lately soooo I figured I’d cheer myself up by drawing my favorite demon mafia men, naturally 💚

This was meant to be just a warm up sketch but 4 hours later and here we are.
Digital fanart by OP of Alessio and Crimson from “Helluva Boss.” They’re standing out on the walkway outside of Crimson’s estate in the Greed ring of Hell. Alessio is glancing down at Crimson with a smirk and Crimson is sort of glancing up at Alessio with a grin. #HelluvaBoss #HelluvaBossAlessio #HelluvaBossCrimson #HelluvaBossCriminAle #HelluvaBossCriminAl #CriminAle #CriminAl #Hellaverse
November 23, 2025 at 1:39 AM
maestropsychopomp.bsky.social
It turns out, you can draw the same idea as many times as you want. 😌❤️

#HelluvaBossCriminAle
#HelluvaBossCrimson
#HelluvaBossAlessio
Many sketched ideas of the same pose: Alessio leaned back on the ground, braced up on his elbows. And Crimson leaning over him, moving towards him on hands and knees. Crimson is looking up at Alessio while saying, "Yer a smart guy. I don't gotta say what this is." Alessio in under Crimson. Alessio says, "Say it anyway." He has a slight blush.
October 30, 2025 at 11:10 PM
Reposted by Maestro Psychopomp
psunnysunq.bsky.social
#HelluvaBoss #HelluvaBossCrimson #HelluvaBossAlessio #Criminales
Crim’s new Halloween look totally stole my heart, so I made this little behind-the-scenes comic!😍
October 6, 2025 at 6:36 PM
maestropsychopomp.bsky.social
Oops! You woke a grumpy Crimson. 💖🤭

#HelluvaBossCrimson
Crimson is lying on his side, his arms and legs are wrapped around a stuffed shark. There's drool on his shark. Crimson looks annoyed and groggy.
October 30, 2025 at 2:48 AM
Reposted by Maestro Psychopomp
psunnysunq.bsky.social
#HelluvaBoss #HelluvaBossCrimson #HelluvaBossAlessio #Criminales
This is the mafia garden gnome I hired with serious money—my succulents are counting on you!!!
September 21, 2025 at 7:13 AM
Reposted by Maestro Psychopomp
witchsyi.bsky.social
Y’know there’s no business before dinner…🚬

I’m so excited to share these pictures with y’all! I’m still working on art but have sum more of the daddy mobster you love to hate 😈💚

📸: kary_filmer on insta

#Crimsoncosplay #helluvabosscrimson #helluvaboss #helluvabosscosplay #helluvabosscosplayer
September 21, 2025 at 9:53 PM
maestropsychopomp.bsky.social
A smoking break can be relaxing. But Crimson is suspicious of the nice feelings he's getting.

#HelluvaBossCriminAle
#HelluvaBossCrimson
#HelluvaBossAlessio
Alessio and Crimson are relaxing on a couch together. Alessio is talking while holding a cigarette. Crimson is smiling with a cigar in one hand and a drink in the other. Alessio laughs. Crimson looks a bit surprised. There's a small heart above his head. Crimson squints suspiciously while smoking his cigar. There's a little heart with a question mark. "Hmm..." is written beside him.
September 20, 2025 at 5:40 AM
Reposted by Maestro Psychopomp
ghostyhaunts.bsky.social
Man that short was so good

I wish Italians were real

😔 🇮🇹 🤌
September 6, 2025 at 7:52 PM