Matthew Sargent
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skippinginfinity.bsky.social
Matthew Sargent
@skippinginfinity.bsky.social
760 followers 350 following 740 posts
Illustrator, Game Designer,
Ska Listener, Pecan Sandy Devourer.

🏁College of the Third Wave
🖍️Book of Coloring +1, +2, +3
🧑‍🎨Halloween + Holiday Wars

linktree.com/skippinginfinity
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skippinginfinity.bsky.social
Matthew Sargent @skippinginfinity.bsky.social · Jul 8
Hey, #PortfolioDay! I'm Matthew, a Chicago-based illustrator working mostly in TTRPGs, where I specialize in character design, maps, and cover art.
Illustration of a flying robotic rob with mechanical tentacles and two of its companions, which have replaced the heads of two mutant bodies, one small and sneaky, one massive and covered in chitin. Drawn for Denizens of the Blood Sands. Black and white isometric dungeon map of a series of caverns populated by goblins, who are shown getting up to all sorts of shenanigans. Drawn for Three Curses for Sister Saren from Planet X Games. Color illustration of a mosh pit of fantasy characters in medieval garb. Rising above them are a purple-haired dwarven woman playing a saxophone and a human man in an aloha shirt, trilby, and checkered tie, carrying a guitar and summoning magical trumpets and trombones. Wraparound cover art for College of the Third Wave. Three black and white cutaway maps of old west train cars, showing the activities of the riders within. Drawn for Sunrise Limited from 321RPG.
Reposted by Matthew Sargent
schweizercomics.bsky.social
Companions of Christmas: MERCURIUS ABU-SIFIN

Today (November 25) is the feast day of this Scythian-Romano soldier saint, who wields two swords: one with which to fight evil men, the other, given to him by the Archangel Michael, with which to fight demons, evil spirits, and monsters. 1/
Watercolored drawing of a romantically fella in a blue Scythian hood and cloak, with light armor and loose trousers, wielding two swords: a grey one and a gold one
November 25, 2025 at 3:48 PM
skippinginfinity.bsky.social
Had a blast playing @dairykillsme.bsky.social’s Thieves of the Tome this evening at PAX Unplugged. Delightfully chaotic!
Photo of my Thieves of the Tome character sheet. Photos of my Thieves of the Tome spell sheet, which uses chapter titles from a book as spell names with the effects made up by me.
November 23, 2025 at 4:04 AM
skippinginfinity.bsky.social
50% survival rate for my peasants in today’s Dungeon Crawl Classics funnel.
Photo of a four-character character sheet for Dungeon Crawl classics. Two of the characters are stamped with the word DEAD in red ink.
November 22, 2025 at 6:43 PM
skippinginfinity.bsky.social
PAX Unplugged, day 1! Tried out Chew for the first time and Pirate Borg for the first time. Much fun was had!
Photo of character sheets for the TTRPG Chew and a board covered in sticky note clues. Photo of the Pirate Borg rule book and character sheet.
November 22, 2025 at 3:19 AM
skippinginfinity.bsky.social
We’ve arrived in Philadelphia and are ready to join our fellow nerds at PAX Unplugged!
Photo of my wife and I standing in the street median in front of Philadelphia City Hall.
November 21, 2025 at 3:46 AM
Reposted by Matthew Sargent
zazb.bsky.social
My comfort zone:
Tiny fantasy people, preferably with big backpacks.
Four types of adventurers from two different settings. The first row reads: Human fighter, Gnome wizard, Earthen Thief, and Svar cleric. The second row is the same archetypes but they are all humans from The Thief of Tales. Three Earthen (a fantasy dwarf-like people) adventurers. They are listed as an Anvil City artificer, a Thoranic Templar, and a Burrow Lancer. This last one is riding a badger. A collection of ancestries from my fantasy setting. An outdated list of classes from the MCDM RPG, Draw Steel. A fan art because I love their game design.
November 14, 2024 at 12:55 PM
Reposted by Matthew Sargent
skippinginfinity.bsky.social
Finally getting the College of the Third Wave band together! Next up: character sheets for these guys.
Illustration of four fantasy musicians in a lineup. From left-to-right is an armored dwarven bass player, a punk rock human drummer, a tiefling singer in a leather jacket and plaid skirt, and a brass dragonborn horn player dressed in a Hawaiian shirt and blowing a fireball through a trumpet.
November 13, 2025 at 4:31 PM
skippinginfinity.bsky.social
Church Doodle Sunday!
Sketchbook page filled with assorted ballpoint pen drawings.
November 16, 2025 at 8:30 PM
skippinginfinity.bsky.social
Finally getting the College of the Third Wave band together! Next up: character sheets for these guys.
Illustration of four fantasy musicians in a lineup. From left-to-right is an armored dwarven bass player, a punk rock human drummer, a tiefling singer in a leather jacket and plaid skirt, and a brass dragonborn horn player dressed in a Hawaiian shirt and blowing a fireball through a trumpet.
November 13, 2025 at 4:31 PM
skippinginfinity.bsky.social
Ever wanted to play the sword instead of the swordsman in D&D?
steveconley.bsky.social Steve Conley @steveconley.bsky.social · 15d
The Kickstarter for my latest 5E zines (plural!) launches today at noon ET. If you’re so inclined, you can check it out here… stabracadabra.com
November 12, 2025 at 4:41 PM
skippinginfinity.bsky.social
If you're into sci-fi TTRPGs, be sure to check out @darkspacerpg.bsky.social! It's Shadowdark in space, and I'll be doing a bunch of fun monster illustrations for it!

www.kickstarter.com/projects/dmi...
DarkSpace - Sci-Fi Rules for Shadowdark
Journey into the shadows and darkness of science fiction for fortune and glory!
www.kickstarter.com
November 11, 2025 at 7:17 PM
skippinginfinity.bsky.social
Church Doodle Sunday!
Sketchbook page filled with assorted ballpoint pen drawings.
November 9, 2025 at 8:00 PM
skippinginfinity.bsky.social
First time my work has been a stamp!
zombiejoe.bsky.social Zombie Joe (Joe Alfano) @zombiejoe.bsky.social · 19d
Our certs, fruit from one of the authors to feed the dungeon masters, and our stamp featuring the art of @skippinginfinity.bsky.social
November 8, 2025 at 11:17 PM
skippinginfinity.bsky.social
Watched Jurassic Park this afternoon. I never noticed before how far from “spared no expense” the ice cream was.
Still frame from Jurassic Park in which John Hammond is eating ice cream from big budget tubs.
November 8, 2025 at 8:26 PM
skippinginfinity.bsky.social
Cover Artists!

QRP with your covers 📖
Cover art for College of the Third Wave. A man in a Hawaiian shirt and checker-banded trilby, carrying a guitar and summoning magical trumpets, leaps above a mosh pit of medieval fantasy characters. Cover art for Quest for Owlbear Milk. An owlbear looks through an empty glass milk bottle, which comically distorts its eye. Cover art for We Are Grung V: Live Grung Hard with a Vengeance. Three anthropomorphic frog men tied to a fire hose leap off the top of an exploding building. Wraparound cover art for Denizens of the Blood Sands. A hulking mutant with many limbs prowls over ruins in a desert, hunting. It has one green-skinned woman in its clutches, and two other humanoid figures hide from it, ready to fight..
November 7, 2025 at 8:39 PM
Reposted by Matthew Sargent
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me. I love bringing these creative character concepts to life, especially when it comes to regulars. Bill and Jessica always have really fun, unique character ideas, and I had a blast drawing their group of beastfolk.
Photo of a man and a woman holding up three pieces of character art. Black and white illustration of an angry anthropomorphic bear wielding a war axe in one hand while making a throwing motion with the other arm, which is a mechanical prosthetic. Black and white illustration of a tabaxi wearing a cloak over leather armor and a bandolier of potions. A pair of goggles sit askew on his forehead, and he holds a crossbow in one hand. Black and white illustration of a leather armor-clad tabaxi leaping through the air, wielding a dagger in each hand, trailing trinkets out of a pouch, and with a wild grin on her face.
November 5, 2025 at 4:29 PM
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me. I love bringing these creative character concepts to life, especially when it comes to regulars. Bill and Jessica always have really fun, unique character ideas, and I had a blast drawing their group of beastfolk.
Photo of a man and a woman holding up three pieces of character art. Black and white illustration of an angry anthropomorphic bear wielding a war axe in one hand while making a throwing motion with the other arm, which is a mechanical prosthetic. Black and white illustration of a tabaxi wearing a cloak over leather armor and a bandolier of potions. A pair of goggles sit askew on his forehead, and he holds a crossbow in one hand. Black and white illustration of a leather armor-clad tabaxi leaping through the air, wielding a dagger in each hand, trailing trinkets out of a pouch, and with a wild grin on her face.
November 5, 2025 at 4:29 PM
Reposted by Matthew Sargent
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me. I love bringing these creative character concepts to life - like this tendril-haired dragon lady for Dave!
Black and white drawing of a humanoid, dragon-like woman with three long tendrils growing from her head reminiscent of suckerless octopus tentacles. She is dressed in a hoodie, t-shirt, and leggings. Photo of a man holding the artwork of his character.
November 4, 2025 at 4:13 PM
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me. I love bringing these creative character concepts to life - like this tendril-haired dragon lady for Dave!
Black and white drawing of a humanoid, dragon-like woman with three long tendrils growing from her head reminiscent of suckerless octopus tentacles. She is dressed in a hoodie, t-shirt, and leggings. Photo of a man holding the artwork of his character.
November 4, 2025 at 4:13 PM
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me, especially when it comes to regulars. This is the 4th time I've drawn @ginnyloveday.com's niece Skylynn. She's been a mage, a rogue, a barbarian, and now a druid now that she has a cat!
Black and white drawing of a girl in a tunic and cloak wearing a cat on her head as if it were a hat. The cat seems okay with it. Photo of a purple-haired woman holding the artwork.
November 3, 2025 at 4:16 PM
skippinginfinity.bsky.social
Church Doodle Sunday!
Sketchbook page filled with assorted ballpoint pen drawings.
November 2, 2025 at 8:21 PM
Reposted by Matthew Sargent
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me, especially when it comes to regulars. This is the 5th time I've drawn @latiajacquise.com's dog Dio, each time as a different D&D class.

This year, Dio became a bard based on heavy metal singer Ronnie James Dio!
Black and white drawing of a anthropomorphic dog, dressed in a loose shirt, throwing up the metal horns with his hands. Photo of Dio the dog next to the drawing of Dio the bard.
October 30, 2025 at 3:16 PM
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me, especially when it comes to regulars. This is the 5th time I've drawn @latiajacquise.com's dog Dio, each time as a different D&D class.

This year, Dio became a bard based on heavy metal singer Ronnie James Dio!
Black and white drawing of a anthropomorphic dog, dressed in a loose shirt, throwing up the metal horns with his hands. Photo of Dio the dog next to the drawing of Dio the bard.
October 30, 2025 at 3:16 PM
Reposted by Matthew Sargent
jontofski.bsky.social
Sybil.
October 30, 2025 at 12:27 AM
Reposted by Matthew Sargent
skippinginfinity.bsky.social
Drawing character art for folks is always a highlight of #GameholeCon for me. I love bringing these creative character concepts to life - like this Goblin Druid and her tiara-wearing polar bear wildshape, a favorite childhood character of Bronwyn. Commissioned by @thomasvalley.com.
Black and white illustration of a goblin girl with a big grin on her face and arms flung open as if waiting for a hug. Lines of magic flow up from her and become a polar bear wearing a tiara, representing her transformative abilities. Pencil sketch of the illustration.
October 29, 2025 at 3:12 PM