Matthew Sargent
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skippinginfinity.bsky.social
Matthew Sargent
@skippinginfinity.bsky.social
750 followers 340 following 730 posts
Illustrator, TTRPG Player, 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.
skippinginfinity.bsky.social
Ever wanted to play the sword instead of the swordsman in D&D?
steveconley.bsky.social Steve Conley @steveconley.bsky.social · 20h
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 · 4d
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
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
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 card-slingin' cowboy (based on @steveconley.bsky.social's Death Dealer rogue subclass) for Rick.
Black and white drawing of a cowboy, eyes in the shadow of a wide-brimmed hat, mischievous grin on his face, wielding playing cards between his fingers. Photo of a man holding the drawing.
October 28, 2025 at 3:11 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 tortle musician and his gremlin companion for Jason!
Black and white illustration of a humanoid tortoise playing a sataer (a long-necked, bowed instrument) while a mischievous gremlin sits atop his shell. Photo of a grinning man holding the drawing of the turtle man.
October 27, 2025 at 3:37 PM
skippinginfinity.bsky.social
Church Doodle Sunday!
Sketchbook page filled with assorted ballpoint pen drawings.
October 26, 2025 at 6:39 PM
skippinginfinity.bsky.social
Got my contributor copies of Denizens of the Blood Sands (handed to me at GHC by @rpg-ramblings.bsky.social himself). This was a super fun project, and the books turned out great!
Photo of two copies of Denizens of the Blood Sands in my hand. Both digest-sized, one hardcover and one softcover. The cover features an illustration of a huge, mutated creature crawling over a ruined structure, seeking the sci-fi warriors hidden inside. In one hand, it has already captured a green-skinned woman. Photo of an illustration from Denizens of the Blood Sands. A robed person stands on a floating platform, casting a spell that is manipulating dozens of metal plates around him. In the foreground, two sci-fi warriors stand ready to battle the mage. Photo of a page from Denizens of the Blood Sands. The page includes stats for a "Lindworm, Great" and an illustration of the creature, which is a long, red, scaly wyrm shooting a stream of green caustic gas from its mouth. A skeleton can be seen inside caught inside. Photo of an illustration from Denizens of the Blood Sands. It depicts three round-bodied, tentacled robots with red screens for faces. One floats on its own, one has replaced the head of a hulking creature covered in chitinous spikes, and one has replaced the head of a green, four-armed creature wielding a spear made of scrap metal.
October 24, 2025 at 3:23 PM
skippinginfinity.bsky.social
I should really know better than to update the driver of something that's working perfectly fine. You don't need to teach a 13-year-old Cintiq new tricks.
October 23, 2025 at 8:44 PM
skippinginfinity.bsky.social
A few photos from #GameholeCon. As always, it was a fantastic show! We had a great time slinging art, playing games, and hanging out with friends old and new.
Photo of my wife and I in front of the Gamehole Con entrance. Photo of a D&D game, complete with battle mat covered in tokens, an iPad with a character sheet on it, and scattered dice. Photo of in-progress drawings of fantasy characters spread across a desktop. Photo of my convention table. On it is a book stand filled with coloring books, comics, and TTRPG zines. Behind it is a banner with my name and an illustration of a ska bard.
October 23, 2025 at 3:39 AM
skippinginfinity.bsky.social
That was a rough one!
Wordle 1,586 4/6
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October 22, 2025 at 3:46 PM
Reposted by Matthew Sargent
skippinginfinity.bsky.social
Gamehole Con commissions.
Photo of five black and white drawings of fantasy characters.
October 19, 2025 at 3:26 PM