Hire Bob O’Brian For Your Party or Event Today!

Caricature Samples

Three unique styles. One unforgettable artist.

Explore Bob’s work below — whether you’re looking for the cutting-edge flair of digital caricatures, a personalized piece created from a photo, or the classic marker-on-paper experience that has entertained crowds for decades. Each gallery below showcases a different style so you can imagine exactly how Bob can bring your next event or gift to life.

🎨 Digital Caricatures

21st Century Caricature Artistry

Looking for something that stops traffic at your tradeshow booth or keeps guests buzzing at your event?
Bob’s live digital caricatures combine timeless artistry with modern technology.

 

  • Drawn on the latest tablets and projected on a large screen for all to see

  • Crisp, full-color caricatures printed instantly as 4×6 keepsakes

  • Digital files emailed to guests so they can post on social media right away

  • Optional branded logos or event names added to every drawing

  • Lanyard ID badge holders available so guests can “wear” their caricature on the spot

This is more than entertainment — it’s a spectacle that gets people talking, sharing, and remembering your event long after it’s over.

Rates start at $225 per hour. All events have a two hour minimum. 

✏️ Traditional Caricatures

Classic, Lively, and Always Fun

There’s a reason traditional caricatures remain a crowd favorite. With just a few quick strokes, Bob creates hilarious, yet complimentary likenesses that everyone loves to take home.

  • Perfect for birthdays, school events, proms, bar mitzvahs, and more

  • 11×17 + 8×10 marker drawings with splashes of color, protected in clear sleeves

  • Fast and interactive — 10 people per hour

  • Always accompanied by Bob’s friendly banter and engaging personality

Rates start at $165 per hour.
All events have a two hour minimum. 

📸 Digital Caricatures From Photo

A Unique, One-of-a-Kind Gift

When you want to give something unforgettable, a hand-drawn caricature from a favorite photo is the answer. Perfect for:

  • Retirement tributes

  • Wedding guest sign-in sheets

  • Group portraits

  • Personalized gifts for coworkers, friends, or family

Each artwork is fully customized to your vision, starting at just $125 with typical turnaround in about a week. Make someone smile with a keepsake that’s personal, playful, and permanent.