The Drawing Room

Kenosha, WI

$175-$250 per hour. depends on scope of event.

Travels up to 0.5 hours

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Caricature Reveal

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Transformed into Avatars Caricature

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Live Drawing

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Sneak Peak of Live Drawing Board

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Caricature Reveal

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Lucille Ball Caricature

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Chicago Event

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Black & White Group Caricature

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Caricature Reveal Northwestern University Event

Overview

New to gig salad but Over 20 years experience drawing caricatures professionally. My style is detailed & a bit on the silly side. Sometimes narrative; unique to comedy writing in my blood. l enthusiastically enjoy caricature entertainment for events because it's a cross between performing comedy & art. They are memorable, spontaneous, hilarious. It's an experience everyone enjoys & relaxes around. It intrigues me that no matter how many faces I have drawn no two people are alike. I enjoy transmitting the personality of someone in a drawing & background gags. I live for the laugh @ the end of a drawing!


Reviews

2 reviews

Small thumbnail image for reviewer David P.

David P.

May 1, 2025
Verified review

An incredible evening with cariactures!

Josie was an absolute pleasure. She was incredibly prompt and was so engaging. Outside of the drawings, people just loved chatting with her while they were getting drawn! I couldn't recommend Josie more for any artist needs.

Hired as: Caricaturist

Small thumbnail image for The Drawing Room

The Drawing Room

Awe ! You’re the best! Thank ya thank ya!


Small thumbnail image for reviewer Brenda K.

Brenda K.

June 11, 2024
Verified review

WOW!!! So much fun!

Josie was wonderful! She engaged our guests in such a fun, personable way, getting to know each person as she drew them. She was professional, courteous, and so gracious! I highly recommend Josie and will hire her again in the future!

Hired as: Caricaturist

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The Drawing Room

Awe! Thank u!!! & SUCH a worthy cause-your gala was. I ended up learning so much from a few of your event heros while I was there! Lovely evening drawing & relaxing together. I’m a lucky ducky to have been invited to draw for it.
❤️ x1000 Josie

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Booking information

Price range: $175-$250 per hour. depends on scope of event.

Languages: English, I Understand Spanish/Speak A Bit!

Gig length: 120 - 360 minutes

What to expect

It's a smooth fun process. I show up early to set up & arrange my chairs/table/art materials. I review lighting or set up my own. I do brief drawing warm up exercises to prepare for the speed of the drawing. If people do not line up right away for one, I let people know directly I'm available. It also helps to avoid the long lines at the end of an event!
Once I'm drawing it's non stop fun for everyone around including myself. When it's time for payment, preferably up front, my only request is make sure this is a detail you know how to handle in advance. It's no fun searching a crowd trying to pinpoint who and when someone will pay you before a long drive back home. Many events have ended with me waiting around. Sometimes I can stay longer for extra pay if the event wants more of my work for longer. It's a beautiful art form and I'm very lucky to say I enjoy every second still after twenty years!

About

I'm a cartoonist with puppeteering background. I drew caricatures for ten years at Navy Pier in Chicago before I opened up my own summer business at the Bristol Renaissance Faire, Wi. which is currently in its eleventh year of business. I was trained around some of the best in the industry and I thank my lucky stars for that every day. I have a dedicated Caricature Art Studio in downtown Kenosha, Wi. called the Drawing Room. This is a place people come for special occasions to be drawn as a caricature, or for social plans. I also own a funky creative optical shop called Rockit Optical Eyewear in Kenosha, Wi. which merges my facial analysis caricature ability to properly style people into unique/custom painted frames. I have completed a stand up comedy internship at The Comedy Bar in Chicago, IL. and take sketch comedy writing classes at Second City. This does inform my style of art. You've been warned! I write poetry and unicycle in my free time. I love animals! They are always welcome to be around me at any gig! ALL of them!

Additional booking notes

Must be as far away from speakers as possible so I can communicate with the people I draw.
I require a table and 5 chairs. I need a small amount of space. Estimation of 5 feet by 3 feet.
I prefer to be near an outlet in case I need to add lighting, I do bring my own extension cord and some form of extra light as needed. But I can live without being near an outlet as well. I improvise well when needed.
Payment needs to be organized. Preferably before I start but after is fine as long as it's prompt. It's not pleasant to be standing around, asking people how to find so and so at the end of a night before a long drive home.
Additional compensated working time can be requested spontaneously during the gig to accommodate extra guests as long as the person paying me requests it and I have nothing else lined up afterwards. I can also do a fee per picture to be charged to the guest directly after allotted gig time is over if that is preferred. I do not stay longer without compensation, or because the crowd asks. The request has to come from the person who is hiring me with the payment added in.

Services offered

Past booked events

November 2025

01

Saturday

Wedding Reception

5:00pm - 7:30pm

Milwaukee, WI

June 2025

18

Wednesday

Children’s Birthday Party

10:00am - 12:00pm

Gurnee, IL

April 2025

30

Wednesday

Cruise Ship Event

7:30pm - 11:00pm

Chicago, IL

September 2024

07

Saturday

Festival

12:00pm - 3:00pm

Wilmette, IL

June 2024

08

Saturday

Nonprofit Event

5:00pm - 7:30pm

Milwaukee, WI

Influences and inspiration

I am influenced by my love of sketch comedy, SNL, Seinfeld. Pearls before Swine comic strip, and the quirks of society. I am also influenced by animals and what I imagine they are thinking as they live alongside of us.

Setup requirements

One table and 5 chairs. That's it! I do the rest. Also must be set up as far away from speakers as possible! So people can communicate to me through the drawing. Thank you!

Lighting is helpful or an outlet for me to be able to plug my own in. I bring my own extension cord.

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