Caricatures and Silhouettes by Leona

Portsmouth, NH

$150 to 400

Travels up to 120 miles

Get a free quick quote
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Leona Caricature Drawing of Mermaid

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Silhouette by Leona

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Silhouette cut in Newberyport, MA.

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Silhouette cut by hand at Spencer-Pierce-Little farm, MA.

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Black and White caricature of two

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Black and White Caricature

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Black and White Caricature of two

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Caricature at Boys and Girls Club in Gardiner, ME

Gallery photo 8 of Caricatures and Silhouettes by Leona
Gallery photo 9 of Caricatures and Silhouettes by Leona

Caricature at Dartmouth College

Gallery photo 10 of Caricatures and Silhouettes by Leona

Superhero Caricature

Overview

My name is Leona Hosack. I am a Silhouettist and Caricaturist. My style of caricaturing has been described as whimsical and flattering! My silhouettes are accurate and flattering as well!
People enjoy watching me cutting silhouettes right on the spot out of black paper! I just look and cut- no tracing or pre-drawing. And when I create a caricature I just look and draw with a permanent marker! No pencil work needed! Each drawing or silhouette is completed in a matter of minutes!

Something new! Virtual Caricature Sessions by Leona! Please contact me for more information.


Reviews

16 reviews

Small thumbnail image for reviewer Ashley S.

Ashley S.

May 13, 2026
Verified review

Excellent Activity for Museum Event

Leona was a fantastic addition to our museum event! We were excited to have a silhouette artist to make a thematic connection to one of our current exhibitions. Our guests were excited to get their portraits done, and were impressed by Leona's skills! We are thankful for her role in making our event a success. Thank you!

Hired as: Silhouette Artist


Small thumbnail image for reviewer Natasha F.

Natasha F.

December 7, 2025
Verified review

Everyone LOVED their characatures!!

Leona did a terrific job at our party! There always a steady stream of people getting their drawings done. Leona was a big hit and was a very hard worker!

Hired as: Caricaturist


Small thumbnail image for reviewer Patrick A.

Patrick A.

October 5, 2024
Verified review

Fantastic!!

Leona was great! She did a terrific job and our wedding guests loved having her! Very easy to work with. Would absolutely book her again!

Hired as: Caricaturist


Small thumbnail image for reviewer Lee K.

Lee K.

April 28, 2024
Verified review

Great job!!

Leona was awesome! Super professional and and great artwork!! Thank you!

Hired as: Caricaturist


Small thumbnail image for reviewer Kira S.

Kira S.

January 24, 2024
Verified review

10/10 Recommend for weddings!

We hired Leona for our wedding reception in January (2024) and she was absolutely amazing! Her caricature style is wonderfully endearing and all of our friends and guests had so much fun sitting for and receiving their portraits! Thank you so much Leona!
-Kira & Brian Leger

Hired as: Caricaturist

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Booking information

Price range: $150 to 400

Languages: English

Gig length: 120 - 240 minutes

Unions: Other

What to expect

It's your choice to have me offer just caricatures or just silhouettes, or both Caricatures and Silhouettes to your guests during your event. I will cut or do as many portraits as I can in the time alloted, and guest will be able to take them home that day! Guests will receive a caricature of themselves on a 9 x 11 piece of quality acid free white card stock, or in the case of two or more subjects they will receive their caricatures on a 11 x 14 piece of bristol board. Silhouettes will be cut of out acid-free black Silhouette paper, and adhered on to a 5 x 7 piece of white card stock. In the case of a double portrait Silhouettes will be placed on a piece of white card stock that will fit in a frame with an 8 x 10 opening.

I love to have people watch me as I cut Silhouettes or draw Caricatures! I love to answer questions as I work and chit chat with onlookers. I specialize in creating fun and flattering portraits while providing a unique and entertaining experience for your guests!My name is Leona Hosack. I am a Silhouettist and Caricaturist. My style of caricaturing has been described as whimsical and flattering! My silhouettes are accurate and flattering as well!
People enjoy watching me cutting silhouettes right on the spot out of black paper! I just look and cut- no tracing or pre-drawing. And when I create a caricature I just look and draw with a permanent marker! No pencil work needed! Each drawing or silhouette is completed in a matter of minutes!

Something new! Virtual Caricature Sessions by Leona!
I will draw caricatures of each of your subjects attending your virtual event, one at a time via Zoom or some other online video chat platform. The caricaturing will take place during a pre-arranged time of 2 hours per session. Your participants will be able to view themselves and their friends being drawn. (10 subjects at the most per 2 hour session)
Your guest can make comments as they watch themselves being drawn by hand in real time. And I will respond and answer questions about my processes and background in being a caricature artist.
An hour after the event, digital scans of your caricatures will be sent to you so you can upload them to any device or print them out. The originals will be sent to you via snail mail on the next business day.

About

My name is Leona Hosack. I am a Silhouettist and Caricaturist. My style of caricaturing has been described as whimsical and flattering! My silhouettes are accurate and flattering as well! I love creating Caricatures or Silhouettes live at special events.

People enjoy watching me cutting silhouettes right on the spot out of black paper! I just look and cut- no tracing or pre-drawing. And when I create a caricature I just look and draw with a permanent marker! No pencil work needed!

Each drawing or silhouette is completed in a matter of minutes! It only takes only five minutes for me to get a good likeness with either Caricatures or Silhouettes! A Silhouette and Caricature Artist can be a real attention grabber and a fun addition to your party!

Some of the events I have been hired for include: Graduation Parties, Historic Houses, Festivals, Splash Parks, Boat Tours, Parties, Bah Mitzvahs, Weddings, Craft Fairs, and Churches, Graduation events and Town Celebrations.

Some of the events I have been a part of as a silhouette or caricature artist include: Sarah Orne Jewett House, Hamilton House, Strawberry Festival, Kid's Day in South Berwick, ME, Alfred Festival, Shaker Hill Apple Fest, in Alfred, ME, Eliot Festival Day, Eliot,ME., Market Fest in York, ME, York Historic Village, York, ME, and Shaker Village in Alfred, ME, Beauport House, Gloucester, MA, Spencer-Peirce- Little Farm, Newberry, MA, Greenfield County Fair in Greenfield, MA, Strawbery Banke, and Jackson House in Portsmouth, NH, Casco Bay Tours, Portsmouth, NH, Liquid Planet in Candia, NH, Fourth of July Celebrations in Portland, ME. I have also done caricatures for Project Graduation events for many schools including St. Joseph's College, ME., Traip Academy in Kittery, ME. and Portsmouth High School, Portsmouth, NH.

I studied Art and Illustration in College and have a Bachelors of Arts Degree from UMASS at Dartmouth. I have always loved drawing faces the most, whether in the form of a realistic watercolor or oil portrait, a caricature or a silhouette!

Additional booking notes

For my Caricature work I usually bring along an easel, but would appreciate having three chairs available. For my Silhouette work again three chairs are all I usually need. Sometimes a small table would be helpful, though not necessary.

Past booked events

June 2026

13

Saturday

House Party

3:00pm - 6:00pm

Sanbornville, NH

May 2026

08

Friday

Nonprofit Event

6:30pm - 9:00pm

Salem, MA

December 2025

06

Saturday

Christmas Party

5:30pm - 9:00pm

Providence, RI

July 2025

13

Sunday

Children’s Birthday Party

3:00pm - 5:00pm

Burlington, MA

October 2024

04

Friday

Wedding Reception

6:00pm - 9:00pm

Portland, ME

September 2024

08

Sunday

Retirement Community Event

12:00pm - 3:00pm

Lexington, MA

July 2024

14

Sunday

Children’s Birthday Party

4:00pm - 6:00pm

Newburyport, MA

May 2024

25

Saturday

Children’s Birthday Party

6:30pm - 8:30pm

Quincy, MA

12

Sunday

Personal Occasion

9:00am - 12:00pm

Newburyport, MA

April 2024

26

Friday

School Assembly

10:30pm - 12:30am (Sat)

Lynnfield, MA

January 2024

20

Saturday

Wedding Reception

1:00pm - 6:00pm

Auburn, ME

October 2023

28

Saturday

Fundraiser

2:00pm - 4:00pm

Scarborough, ME

07

Saturday

Bridal Shower

12:00pm - 2:00pm

Dunbarton, NH

April 2023

22

Saturday

Wedding Reception

5:30pm - 8:30pm

Jackson, NH

November 2022

12

Saturday

Birthday Party

6:30pm - 7:30pm

North Chelmsford, MA

October 2022

29

Saturday

Halloween Party

2:00pm - 4:00pm

Scarborough, ME

September 2022

25

Sunday

Children’s Birthday Party

1:30pm - 3:30pm

Atkinson, NH

17

Saturday

Bridal Shower

4:00pm - 6:00pm

Woburn, MA

July 2022

16

Saturday

House Party

12:00pm - 4:00pm

Wilmot, NH

June 2022

11

Saturday

Prom/After Prom Party

6:00pm - 8:00pm

Somersworth, NH

10

Friday

Graduation

8:00pm - 12:00am (Sat)

Cape Neddick, ME

May 2022

01

Sunday

Wedding Reception

7:00pm - 10:00pm

Manchester, NH

April 2022

13

Wednesday

Personal Occasion

10:00am - 10:30am

Milton, MA

09

Saturday

Children’s Birthday Party

2:30pm - 3:30pm

Kingston, NH

October 2021

16

Saturday

Wedding Reception

6:00pm - 9:00pm

Fall River, MA

August 2021

21

Saturday

Wedding Reception

3:00pm - 5:00pm

Moultonborough, NH

March 2020

14

Saturday

Teen Birthday Party

7:00pm - 8:30pm

Bedford, NH

December 2018

29

Saturday

Children's Birthday Party

4:00pm - 5:30pm

Haverhill, MA

September 2018

15

Saturday

Nonprofit Event

3:30pm - 6:30pm

Newburyport, MA

October 2017

21

Saturday

Reunion

1:00pm - 4:00pm

Portland, ME

May 2017

31

Wednesday

Anniversary Party

12:00pm - 12:15pm

Epping, NH

July 2016

30

Saturday

Birthday (Child)

5:00pm - 8:00pm

Seabrook, NH

June 2016

03

Friday

Graduation

11:30pm - 1:30am (Sat)

Dover, NH

June 2015

28

Sunday

Bar/Bat Mitzvah Party

11:00am - 3:00pm

Winchester, MA

October 2014

25

Saturday

Birthday Party

3:00pm - 7:00pm

Newburyport, MA

June 2014

11

Wednesday

Other

4:00pm - 8:00pm

Freeport, ME

Influences and inspiration

I have had many chances to look at traditional silhouettes cut in the 18th and 19th centuries at some of the historic houses where I have cut Silhouettes, and I have enjoyed trying out some historic methods, including hollow cut silhouettes. I have also been inspired by the silhouette work of Charles Burns in Great Britain. In terms of Caricatures I have always loved the work of Al Hirschfeld!

Setup requirements

All I need for either Caricatures or Silhouettes are three chairs. Some times a small table would be helpful, though not necessary.

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