Matthew Sargent
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skippinginfinity.bsky.social
Matthew Sargent
@skippinginfinity.bsky.social
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
Pinned
Hey, #PortfolioDay! I'm Matthew, a Chicago-based illustrator working mostly in TTRPGs, where I specialize in character design, maps, and cover art.
Ever wanted to play the sword instead of the swordsman in D&D?
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
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
Church Doodle Sunday!
November 9, 2025 at 8:00 PM
First time my work has been a stamp!
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
Watched Jurassic Park this afternoon. I never noticed before how far from “spared no expense” the ice cream was.
November 8, 2025 at 8:26 PM
Cover Artists!

QRP with your covers 📖
November 7, 2025 at 8:39 PM
Reposted by Matthew Sargent
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.
November 5, 2025 at 4:29 PM
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.
November 5, 2025 at 4:29 PM
Reposted by Matthew Sargent
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!
November 4, 2025 at 4:13 PM
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!
November 4, 2025 at 4:13 PM
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!
November 3, 2025 at 4:16 PM
Church Doodle Sunday!
November 2, 2025 at 8:21 PM
Reposted by Matthew Sargent
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!
October 30, 2025 at 3:16 PM
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!
October 30, 2025 at 3:16 PM
Reposted by Matthew Sargent
Sybil.
October 30, 2025 at 12:27 AM
Reposted by Matthew Sargent
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.
October 29, 2025 at 3:12 PM
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.
October 29, 2025 at 3:12 PM
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.
October 28, 2025 at 3:11 PM
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!
October 27, 2025 at 3:37 PM
Church Doodle Sunday!
October 26, 2025 at 6:39 PM
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!
October 24, 2025 at 3:23 PM
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
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.
October 23, 2025 at 3:39 AM
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
Gamehole Con commissions.
October 19, 2025 at 3:26 PM