Designs by Dennis Caricatures

East Weymouth, MA

$75-$125

Travels up to 1.5 hours

Get a free quick quote
Promotional video thumbnail 1 for Designs by Dennis Caricatures

Dorchester Brewing

Promotional video thumbnail 2 for Designs by Dennis Caricatures

Boston college club private event.

Promotional video thumbnail 3 for Designs by Dennis Caricatures

Millis HS Graduation breakfast

Promotional video thumbnail 4 for Designs by Dennis Caricatures

Millis HS Graduation Breakfast

Promotional video thumbnail 5 for Designs by Dennis Caricatures

Millis HS Graduation Breakfast

Gallery photo 1 of Designs by Dennis Caricatures

Live color caricature

Gallery photo 2 of Designs by Dennis Caricatures
Gallery photo 3 of Designs by Dennis Caricatures
Gallery photo 4 of Designs by Dennis Caricatures
Gallery photo 5 of Designs by Dennis Caricatures
Gallery photo 6 of Designs by Dennis Caricatures
Gallery photo 7 of Designs by Dennis Caricatures
Gallery photo 8 of Designs by Dennis Caricatures
Gallery photo 9 of Designs by Dennis Caricatures
Gallery photo 10 of Designs by Dennis Caricatures

Overview

Note: gigsalad takes a % of the gross. You can book direct thru me.
For the last 20 years I’ve been entertaining the masses up and down New England and throughout many states in North America. I use my background in fine art, architecture, and comic book illustration to draw up caricatures for some truly amazing organizations and individuals. Clients such as The Boston Red Sox, New England Patriots, numerous Ivy League colleges & universities, as well as some musical acts such as Coldplay and The Lumineers, have helped me craft speed, humor & quality into all my artwork. I average 2-4min (b/w) & 5-7min per face (color). Please give a look at my Instagram @DesignsbyDennis. Commissions open.


Reviews

Be the first to review Designs by Dennis Caricatures

Write a review

Booking information

Price range: $75-$125

What to expect

You’ll never be bored in the chair across from my easel. I make it point to ensure anyone I caricaturize is alway being interacted with. Those 5-10min is the opportunity to learn about someone and make an impact. The artwork is a bonus to an incredible experience you share with someone. A positive memory last a long long time. Usually the laughs heard coming from my easel bring the masses to get drawn. I thoroughly enjoy making people
Laugh.

About

I studied architecture and illustration at Wentwork Institute of Technology and at the Massachusetts College of Art from (phone number hidden)0. Also, I’ve worked at the art director for Stonehill college theater department. Served as the IT manager from (phone number hidden)9 for the Boston Red Sox. In addition from (phone number hidden)3 I was an entertainer/live caricaturist during all home game for the Red Sox as well (thus, I’m no stranger to large crowds).

Past booked events

May 2025

26

Monday

Wedding Reception

5:00pm - 8:00pm

Gloucester, MA

15

Thursday

Personal Occasion

1:30pm - 3:00pm

Plymouth, MA

June 2024

22

Saturday

Children’s Birthday Party

11:00am - 1:00pm

Boston, MA

Check out these featured profiles

Featured

Boston Casino Events

1 Verified booking

  • Danvers, MA
  • Casino Party Rentals
  • $300-$100,000

Entertainment/party rentals, specializing in Casino, Corporate and family parties of all types. You must visit our web site to see the unlimited things that...
Featured

Kaleidoscope Artistic Entertainment

4.81 (158)
Top Performer
330 Verified bookings

  • Hartford, CT
  • Children’s Party Entertainment
  • Contact for rates

Francisco V. said “Kaleidoscope did an amazing job entertaining the little ones for our Easter Brunch. ”

Dave MacDonald

4.92 (145)
Top Performer
382 Verified bookings

  • Chelmsford, MA
  • Caricaturist
  • $100 to $150 a hour

Megan R. said “We had a small “corporate” event of about 60ish people. Dave banged out tons of portraits for my employees and they all loved it! 10/10 recommend Dave and will hire again when needed. Thanks Dave! ”