Pre-Filibuster cartoons
Though I’ve always been interested in cartooning, it took me a while to get turned onto political cartooning in particular. Like many, I initially regarded editorial cartoons as an extremely stiff and uninteresting genre, dominated by uptight, unfunny depictions of overly crosshatched big-head-small-body politicians and cryptic visual metaphors of uninteresting political issues.
My thinking only really changed as a result of a growing interest in caricatures. After being introduced to the brilliant flash web series “Like, News” featuring the loose and highly stylized caricatures of Don Asmussen, I realized that drawing funny pictures of famous people could actually be a lot more fun and creative than I originally thought. So I abandoned my previous artistic obsession, which had been drawing video game characters, and embraced a new one.

Some of my early caricatures. Like most artists just learning how to draw caricatures, the temptation was to mainly focus on people who already had very wacky faces to begin with.
Eventually I began to realize that in order to have my caricatures do interesting stuff, rather than just be floating heads, I would have to learn about politics. So I started watching the news more actively, and here we are.
This is my first-ever political cartoon, drawn when I was about 16. Texas Governor George W. Bush had just announced that former Congressman and Secretary of Defence Dick Cheney would be his running mate, which was slightly controversial because of Cheney’s supposedly hard-right voting record in the House of Representatives.

Here’s another one I remember being quite proud of at the time. It’s supposed to depict Bill Clinton failing to get Ehud Barak and Yasser Arafat to come to a peace deal in the final days of his presidency:

The founding of Filibuster
When I was in the eleventh grade, way back in early 2001, I took a marketing class that entailed designing a personal website. Though I had dabbled with making personal websites before, the technology was still fairly primitive and confusing. There were none of your fancy WordPresses and Bloggers in those days, just crude HTML editors — or so I thought. The class introduced me to Yahoo! SiteBuilder, which was this extremely easy drag-n-drop operation. When I got home, I decided to use the same editor to make a new site to launch my new career as an editorial cartoonist.
I called my site “Filibuster” after the parliamentary debating tactic, which, in those more innocent times, was still still somewhat obscure and arcane. Of course, now everyone filibusters everything all the time, so the name has lost a lot of the cryptic appeal I originally intended.
The evolution of the site
Unfortunately, the Wayback Machine doesn’t have any documentation for the SiteBuilder phase of Filibuster, which, truth be told, only lasted a couple of months. Since then, the site has gone through three distinct looks:

