Designs by Dennis Caricatures

Designs by Dennis Caricatures Local caricaturist from Boston. Helping the people laugh. One drawing at a time.

Next weekend the studio is headed to Trumbull CT.. for New England Fan Con. I’ll be sharing more details soon…. August 1...
08/09/2026

Next weekend the studio is headed to Trumbull CT.. for New England Fan Con. I’ll be sharing more details soon…. August 15-16, 2026
Trumbull Marriott Shelton Trumbull, CT…

Now.. Connecticut and I have not exactly seen eye to eye …ever. But I’m certainly now willing to let bygones be bygones….

Reboot weekend. Let’s go!

https://nefancon.com

This Friday and Sunday the studio aims to doodle up some four legged friends at the and maybe some human folk too 😉 for...
08/06/2026

This Friday and Sunday the studio aims to doodle up some four legged friends at the and maybe some human folk too 😉 for a doggo themed event! I’ll be setup with a few other mom & pop pet vendors. Tunes and brews are on tap for the evening. So swing by this hidden gem in Quincy/Wollaston for a some laughs and howls!! Also I am VERY warmed up to draw up your doggos! Taking commission orders and live as well! Drop me a DM for more info! Sponsored by Widowmaker Brewing

07/25/2026

I really love doing this style of caricature, I just wish it wouldn’t take so damn long (I’m sure there are shortcuts I need to learn). In an age where everything is “oh thats AI or a filter, or for the elder folk, oh thats photoshop’d”, I make a pencil sketch of EVERY face I draw before I run it thru any drawing app. Keeping it still traditional, prior to importing it into 21st century tech. Gotta learn the face before any digital edits happen. I like being old skool, even with all these new bells and whistle features of Procreate. It’s the polish and completeness that I really love about it.

May need to continue down my rabbit hole of illustrating classic actors and actresses from years ago. And can we all agree Audrey Hepburn was absolutely stunning, sweet fancy Moses with roses.



I’ve a secret offer on this same post on my Instagram acct.

Audrey.
07/24/2026

Audrey.

07/14/2026

This Saturday at the Natural Resources Trust (NRT) Sheep Pasture in Easton Ma. I’ll be setup from 10-2pm drawing all the peoples and fur babies. Come enjoy a great day with your dogs and other mom & pop shops, live music, food, and ME the cave painter! Prices are listed above. Commissions are the best option to get a solid quality piece of artwork done of your family dog, cat, or,,,, bull.. present by the .

This Saturday at the Natural Resources Trust (NRT) Sheep Pasture in Easton Ma. I’ll be setup from 10-2pm drawing all the...
07/14/2026

This Saturday at the Natural Resources Trust (NRT) Sheep Pasture in Easton Ma. I’ll be setup from 10-2pm drawing all the peoples and fur babies. Come enjoy a great day with your dogs and other mom & pop shops, live music, food, and ME the cave painter! Prices are listed above. Commissions are the best option to get a solid quality piece of artwork done of your family dog, cat, or,,,, bull.. present by the .

Face painting is fun, but washes off.. Airbrush tattoos last a few days (maybe a week)..Balloons lose their air after a...
07/09/2026

Face painting is fun, but washes off.. Airbrush tattoos last a few days (maybe a week)..
Balloons lose their air after a day or 2 (or even burst!)..

All great ways to entertain the kids and individuals, but there’s one truly unique form of entertainment that lasts FOREVER, a caricature.

I’ve been drawing caricatures for 20 years and specialist in all sorts of events. Birthdays, weddings, corporate gatherings, festivals, fairs, honestly any event I’ve got you covered. Commissions are always open and not just for human. I can immortalize those fur babies too! Dogs, cats, ducks (yes I’ve drawn ducks)! Numerous options available. Can work from photos. Live caricatures take 2-5min per face. Digital caricatures also available!

Now booking (and looking) for events of all types. Drop me a line! I’ll bring the markers, you bring the faces… or doggos 😉 Designs by Dennis Caricatures [email protected]

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Boston, MA

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