Keeping a comic going for 20 years is an accomplishment in itself, but Tom the Dancing Bug creator Ruben Bolling can't seem to stop dunking on 2017. The law degree-toting cartoonist who made his debut in law school recently took home both the Herblock Prize and a Reuben Award, commemorating two decades of irreverence in syndication. During this time he's created hundreds of freeform comics and authored two all-ages Emu Club graphic novels -- all while holding down a day job and raising a family with his wife. We wanted to ask how he's accomplished all of this, but fearing what would surely have been a diabolical answer, we instead got in touch to inquire about his storied comics career.

GoComics: This year marks Tom the Dancing Bug's 20th anniversary in syndication, but it actually turns 31 this year having debuted in The Harvard Law School Record in 1986. What do you remember about creating your first comic and any reaction it may have gotten?

Ruben Bolling: I loved comics and had tried to be a cartoonist before, but the comic strips I tried to draw were all derivative, boring and unfunny. When I saw a "Cartoonist Wanted" ad in the school newspaper, and I drew that first Tom the Dancing Bug, it was the first time I was able to convey my natural sense of humor onto a comics page. I found my voice, and it was as sudden as getting hit on the head with a 2x4. It was a pretty thrilling moment, and it changed my life.

GC: In addition to cartooning, you've had a successful career in law and financial services. How have your day jobs informed your worldview and work ethic as a cartoonist?

RB: Not in the least. I have two separate jobs, lives, and names, and they never interact.

GC: Tom the Dancing Bug touches on everything from general philosophies to specific state policies, which can prove controversial. Have you ever felt like you've gone too far (or not far enough) expressing your views in your work?

RB: I really don't gauge whether I've gone too far or not far enough. To the extent I judge how I expressed a view, I judge whether or not I expressed it in a funny, entertaining, interesting way. 

GC: There's a narrative that the political climate in the US and other parts of the world is more volatile than ever, particularly as it's expressed with evolving technologies like social media. What's your take, having observed and participated in it as a cartoonist with a political bent over the past three decades?

RB: I don't think I've ever seen a political climate as volatile as it is right now. Seems to me that when I started Tom the Dancing Bug professionally in 1990, the differences between the two parties were relatively minor. Today, you've got the Right trying to take the New Deal off the table, and take us back to Industrial Revolution-era policies.

GC: You've won a lot of awards at this point, including your most recent Herblock Prize and Reuben Award. What does this kind of recognition do for you as a professional cartoonist? Are there any other awards you're still coveting?

RB: I'd make room on the mantle for an Astronaut of the Year. An MTV Award for Best Kiss. Pretty much any award from J.D. Power and Associates.

GC: Working as a cartoonist can open up a lot of opportunities to meet influential people -- heroes, peers, fans. What are some cool experiences you've had through your work in comics?

RB: Getting to meet, and even becoming friendly with, some of my childhood heroes, like Al Jaffee and Garry Trudeau, has been one of the great joys of my career.

But becoming buddies with a group of cartoonists all growing up through the alternative newspaper scene in the 90s has been a blast. People like Tom Tomorrow, Ted Rall, Derf and many others. For a while, we'd all gather at the annual alternative newspaper conferences, because we were self-deluded enough to think we were a part of the industry. We'd run around causing mischief like a bunch of Shriners at a convention. There are a lot of gratifying things about being a cartoonist, but hanging out with this group was one of the only times it was fun.

And I always love meeting readers at conventions and events. But I really treasure the relationship I have with readers in my INNER HIVE subscription service, where I have a direct relationship with the people who enjoy Tom the Dancing Bug. That's been enormously satisfying.