Creative License: The Political Art of DonkeyHotey

December 5, 2014

I learned about the caricatures by DonkeyHotey when I saw one of the artist’s creations on the Constitutional Law Profs Blog. Someone remarked on an illustration of Supreme Court Justice Sonia Sotomayor and I was intrigued. I looked on the DonkeyHotey Flickr photostream, where the images have received over five million views, to find out more about the artist. There wasn’t any additional info. So, I went in search of the mysterious illustrator known only as DonkeyHotey. Following is a slightly edited version of our email interview.

Q: What inspires you as an artist?

A: I feel I am more compelled than inspired. I first started doing cartoons in Photoshop during the Bush 42 administration in response to events. At that time I wanted to comment on what I thought was a lack of honesty in the media coverage of events after 911 leading up to the Iraq War and the War on Terror. George Orwell’s predictions of a dystopian society were coming true. We were moving towards never ending war against ill-defined groups of terrorists abetted by a controlled media and cowed citizens under constant surveillance. Combine those concerns with the real loss of income and opportunity for average Americans in the last forty years and you should understand what inspires me. These trends have not been substantially reversed under Obama. Obviously, life in America is not as bad as Orwell’s vision or I would not be able to express my opinions. My goal is to help avoid that end and move towards a society where we get to enjoy all of our rights ensured by the Constitution.

Q: What is your artistic (and other) background/training?

A: I have no formal training, but I have spent a lot of time working on cartoons and caricatures. Malcom Gladwell claimed “researchers have settled on what they believe is the magic number for true expertise: ten thousand hours.” My goal is to keep working on adding hours to the ledger and to keep improving. At first I drew a lot of caricatures with pencil, pen and ink. Then I stopped doing cartoons for a while due to restraints on my time. When I came back to it around 2008, I had acquired skills with Photoshop, so I just started drawing with it.

kennedy caricature

Q: Why have you chosen caricature as your expressive medium?

A: I have always appreciated illustrations and cartoons. As a child, my family had some old books with illustrations that fascinated me including a copy of Alice In Wonderland, illustrated by John Tenniel; Poems of Childhood, illustrated by Maxfield Parrish, and a series of children’s stories and fairy tales. These all had illustrations that made an impression on me. A spot illustration in a book not only supported the telling of a story, but also was complete on its own. These ideas have drawn me to want to present my work in an editorial context, in that I am offering my cartoons for writers to use to support their posts online. It would be gratifying to be able to produce cartoons that not only communicate a message instantly, but also would also pull people into them and encourage them to consider the more complicated idea. This is something that would make a lasting impression and be relevant years later. I have been building a website, Opinionated Art, where I am collecting information about early caricature artists and cartoons. This has been helpful to me in broadening my understanding of political cartoons.

Q: Do you work in other media? If so, where can we find your work?

A: I only create images in Photoshop, primarily for use by writers to use with editorial content online. The originals are much higher resolution than I post online, so they could be used in print. I have done some work for print including a cover for a book about Ayn Rand, a cover for Utne Reader magazine, and comedian Jimmy Dore used some of my work in his funny new book, Your Country Is Just Not That Into You. My preference is to do work for publication online, but I have a fantasy where some eatery in Washington DC near the Capitol will decide to decorate their walls with my work.

sotomayer caricture

Q: Will you discuss your interest in certain subjects (for us the legal figures are especially relevant, but also political figures)?

A: I am interested in politics and the policies politicians act on to help or hinder the wellbeing of citizens. Politics is not something that happens in the passive voice. Real people are making decisions, writing legislation and enforcing or not enforcing the laws. Those are the people I want to caricature. I hope to express my opinions of their actions in my work. Our politicians put on a show in the media to focus our attention on themes that help support their larger goals. All the shouting and name-calling is the atmospherics masking the real actions that are happening behind closed doors. For example: All the hullabaloo before and after the passing of the ACA masks the reality that it is a welfare program for the Insurance and Drug industries. The negotiations between the Obama administration and those industries were given very little attention in the media. Instead we talk about death panels, the awful website launch and the 100th vote to repeal the bill. I try to have caricatures available on all the top political actors in the news. To that end I caricature politicians, but I also have all the current members of the Supreme Court, the Attorney General and other people directly involved in the courts and law. I comment on legislation and international agreements such as ACTA, CISPA, SOPA, PIPA, the TPP and etc. I have seen many of my works used on legal blogs and websites.

Q: How do you decide who to caricature?

A: I get up every day and start reading the news and listening to podcasts. I don’t have much use for TV and I don’t currently subscribe to a print newspaper. One of my favorite starting points for news is Memeorandum. They aggregate the top news stories from around the web using some algorithm or method that produces what I find to be a reliable view of the most important current events. I follow stories from there to all the usual suspects and occasionally an obscure source. When I draw I listen to audio programming including books from Audible and the public library. I also listen to many podcasts including Sam Seder’s Majority Report, The Jimmy Dore Show, This Week in Law, The Federalist Society, and others. I find the Federalist Society podcasts very engaging when they host a debate and bring in opposing points of view. Most of the time it is very informative to see what Conservative activists are thinking. All this input helps me keep aware of what the top stories and issues of the day are and who the actors involved in those events are. I also know that it is important to have all the top politicians, judges and world leaders. To that end I have a list of positions I try to keep current with such as the Presidents top cabinet and the G20 leaders. This has been my approach so far.

Q: You are anonymous, right? Will you tell me about that?

A: At the time I started it was pretty common for posters online to use a pseudonym. I was attracted to that idea and naively romanticized about continuing the spirit of the Founding Fathers who used pseudonyms to write the Federalist papers including Publius, Cato and others. I started doing that and have continued.

Q: Why do you choose Creative Commons as a way to “distribute” your work? Is there an alternative way you distribute – that pays for your time?

A: When I started doing caricatures in Photoshop there was a lot of talk in the media about the Remix culture. I was noticing people mixing up photos, adding captions or speech bubbles and posting them online to amuse people. This is happening even more today on Facebook and other social media. I started trying to do that and gravitated toward creating caricatures for the subject’s head and then mixing that with other photo sources including my own photographs for bodies and backgrounds and sometimes elements created in Photoshop. My current work is now a combination of caricature, photo collage and photo manipulation. At first I was posting the work to PhotoBucket. Then one day I had one of my images taken down under the Digital Millennium Copyright Act. That image included a screen capture from a CNN show. Then I had another one taken down of Joe Lieberman where I put Lieberman’s head on Borat’s body. You remember the picture of Sacha Baron Cohen wearing an ugly and revealing yellow one-piece bathing suit? That was frustrating to me because I thought I was covered under fair use and First Amendment. I was seeing images like this being posted everywhere, and really even today, I don’t know what the rules are. I am not a lawyer. That led me to do some reading about copyright and Creative Commons. Flickr has made it easy for people publish their work under Creative Commons so I decided to move there in 2010. It seemed to me that I could remix images under certain Creative Commons licenses and in the public domain and then publish them under Creative Commons. I provide attribution and links to my sources. Sometimes I can’t find an appropriately licensed source. In those cases I will create an entirely original painting for the face. That takes longer, but with practice those works are getting better and quicker to produce. I find that Flickr is a good place to be discovered by people searching for images. I have nearly six million views on Flickr. Work from my Flickr photostream has been used to illustrate many posts in online publications including: Daily Kos, Eclectablog, Esquire, Mother Jones, The Guardian, Truthdig, Reason, and many more. I document some of those uses at

Robert Mccullough Hands up

Q: Do you have a “day job”?

A: I am in a situation where I can spend a lot of time creating caricatures. My ultimate goal would be to be hired by an Internet publication to create caricatures, cartoons and covers for digital works. In that fantasy, I would probably stop publishing on Flickr and be exclusive and part of a team. Other possible outcomes I think about include creating a social media site for people doing the same thing that I do.

Q: Anything additional you’d like to tell our readers, or for them to know about you and/or your work?

A: My process is that I find the highest resolution appropriately licensed image I can of the person I want to caricature. I use Photoshop, and in about five to six hours, produce a caricatures at 300ppi and about 8×10 inches. Then I either use the body and/or background from the same image, or find another appropriately licensed photo, or use one from my own library. I put the head on the body in at least two images, one horizontal and one vertical. These are all in layers so I can remix them later. I publish the caricature as described on Flickr. Then, I can pop the head into a new situation. Sometime I will change the expression.

Images: Hillary Clinton, DonkeyHotey/Flickr; Anthony Kennedy, DonkeyHotey/Flickr; Sonia Sotomayor, DonkeyHotey/Flickr; Hands Up Didn’t Indict, DonkeyHotey/Flickr