Drawing all across New England! I can draw you LIVE in 5 minutes or less, fit up to 6 faces in one image, and offer you an array of services such as airbrushed color, black and white. I service all types of events in New England such as the following…
Caricatures for:
Birthdays 🎂
Weddings 💒
Graduation parties 👨🎓
Corporate events 👩🏫👨🏫
Reunions 👨👩👧👧
Community gatherings 👨👩👦👦
And more!
Overview
Hired 159 times
Background checked
1 employee
8 years in business
Business hours
This pro hasn't listed their business hours.
Payment methods
This pro accepts payments via Cash, Check, Credit card, PayPal, and Venmo.
Top Pros are among the highest-rated, most popular professionals on Thumbtack.
2025
2023
2020
Services offered
Type of caricature
Full color
Spot color
Black and white
Event type
Birthday party
Festival
Wedding
Corporate event
Projects and media
Projects and media
Reviews
Customers rated this pro highly for work quality, professionalism, and responsiveness.
Great 4.8
113 reviews
5
92%
4
3%
3
0%
2
1%
1
4%
Your trust means everything to us. Learn about our review guidelines.
Read reviews that mention:
Nealia H.
Jul 25, 2026
•
Hired on Thumbtack
Jay was SO great at our daughter’s birthday party. The caricatures were absolutely amazing. So fun and such style. Everyone loved Jay and our daughter asked if he could come back every year. Thanks, Jay!!!
Details: 25 guests or fewer • Birthday party • Black and white
Caricaturing
India B.
Jun 24, 2026
•
Hired on Thumbtack
Jay is an amazing Caricature artist. He was a big hit at my wedding and all of his drawings were spot on. After doing some research on other local caricature artists, I found his prices to be reasonable. Jay was also friendly, professional, and punctual. I would definitely hire him again and would recommend him for your next event.
Details: 51 - 100 guests • Wedding • Black and white
Jay's Portraits's reply
Thank you for having me!
Caricaturing
Cammie C.
Aug 24, 2025
•
Hired on Thumbtack
Had a party of 30 guests for my husband’s 50th and Jay was the highlight of the night. Jay arrived early and drew nonstop for the three hours booked. Everyone had a memorable souvenir to take home. Some guests even went for second drawings. I opted for black/white caricatures with sleeve protectors. He’s communicative and skillful. Highly recommend his service and would certainly hire him again for future events.
We hired Jay as a feature in our conference booth; attendees would get a memorable caricature drawing from the event, and it gave them something fun to do while we chatted with them about our technology services.
Jay took time to engage with my team, potential clients, and other booth exhibitors to understand the purpose of the conference so he could chat up anyone who sat down for a drawing. We didn't ask him to do this; he took it upon himself.
I fully endorse this dude and suggest you book him for your event.
Details: 26 - 50 guests • Corporate / office event • Black and white
Jay's Portraits's reply
I appreciate you so much for having me be apart of the team and I hope you enjoyed Boston!
Caricaturing
Lynne A.
Nov 23, 2025
•
Hired on Thumbtack
Jay was wonderful! All of my guests who had their portrait done raved about how much fun they had! The laugh alone, I wish I had video to share! He was was very generous with his time! I would absolutely recommend him to anyone looking to enhance their event!
What is your typical process for working with a new customer?
Customers should share details about the project , such as:
*Who’s birthday is it?,
*When and where?
*How many guests are you expecting?
*Do you have any special requests?*
What education and/or training do you have that relates to your work?
As of August 2023 I will officially be able to say I am a student of the great MAD Magazine Caricaturist, Tom Richmond!
How did you get started doing this type of work?
Through my work experience with the YMCA, I began sharing my interest in the arts and it blossomed into opportunities I capitalized on and expanded to create services through the arts.
