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Jay's Portraits

$150/hour
Estimated price


Scheduling

Responds in about 49 min


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If you hire this pro, you’re covered by a money-back guarantee. Learn more

About
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, paper or iPad digital caricatures with prints. 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 154 times

5 similar jobs done near you

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.

Social media

Instagram

Top Pro status

Top Pros are among the highest-rated, most popular professionals on Thumbtack.

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2025

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2023

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2020

Services offered
Type of caricature
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

108 reviews

5

92%

4

3%

3

0%

2

1%

1

4%

Read reviews that mention:


pro avatar
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.

Details: 26 - 50 guests • Birthday party • I'm flexible • I'm flexible

Jay's Portraits's reply
Thank you Cammie!
Caricaturing
pro avatar
Jack W.

Jul 22, 2025

Hired on Thumbtack

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
pro avatar
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!

Details: 51 - 100 guests • Birthday party • I'm flexible

Caricaturing
pro avatar
Chris G.

May 24, 2025

Hired on Thumbtack

I almost don’t know where to begin. Very personable, fun and a heckin good artist. Jay’s work brought us laughs and memories to our graduation party. Excellent experience and a welcomed quirky way to celebrate someone you love. Added bonus: his karaoke skills! Thanks for the traveling and sticking out the rain with us ✌️🎉

Details: 25 guests or fewer • Special event / party • Spot color

Caricaturing
pro avatar
Melissa R.

Dec 14, 2025

Hired on Thumbtack

My guests loved Jay’s work and commented on how nice he was. His drawings were great and they added a fun activity to my annual holiday party.

Details: 26 - 50 guests • Special event / party • I'm flexible

Caricaturing
Credentials
Background Check

Jameilen Jones

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