image preview

Creation Date



Subject of illustration:

Cited by O, the Oprah Magazine as “one of our favorite creative thinkers,” Dion Flynn is a writer, keynote speaker, improvisor, comedian, actor and U.S. Army veteran. He’s best known for playing Barack Obama and other characters and has appeared over 100 times on The Tonight Show Starring Jimmy Fallon. If Dave Chappelle and Eckhart Tolle had a son, it would be strange looking — and so is Flynn. He uses fun and innovative ways to help people connect with themselves and others, leading business professionals, writers, storytellers, college students, salespeople, and recovering and non-recovering folks through his dynamic improvisor-mindset workshops.

Artist's Note

Dion Flynn makes a living from changing his look and face, so there is really no one definitive look for him. It’s also tricky drawing very handsome men, and he has a great smile.


Copyright © 2022, Bob Eckstein. All rights reserved.


Image Location