Jimmy Tingle's down-to-earth and approachable style has helped him perform his political and satirical comedy and get big laughs even from those who disagree with him. He has appeared as a commentator on PBS, NBC, MSNBC, CNN, and the BBC. He was the weekly humorist on 60 Minutes II. He even owned his own comedy theater, and he has appeared in the films Next Stop Wonderland and Head of State.

When did you first realize that you were uniquely funny?

When you asked me to contribute to this book.

Who do you think were your influences?

Daniel Boone, Lenny Bruce, my mother.

Do you remember your first original joke?

Yes, but I cannot repeat it here. My first real material was song parodies that I would perform in a trench coat, sunglasses, and felt hat, a la The Blues Brothers. I was trying to be the comedian with the blues and I had several songs; “Thank God I'm a City Boy” and “Thank God I'm a ‘Burbite” were takeoffs on the John Denver “Thank God I'm a Country Boy.” “The Test Tube Baby Blues” was in response to the birth of the first test tube baby, and “The Pooper Scooper Blues” was a protest song against the newly enacted pooper scooper legislation, which I opposed. Looking back on it I realize I was actually advocating for poop on the sidewalk.

When did you realize that comedy was something you had to do for a living?

When I first performed on Lenny Clark's open-mic night in 1980. Forty friends showed up and after I was done with all my songs, they cheered wildly. The rest of the audience was probably cheering just because the songs were over, but regardless — I was hooked.

What was your first job in comedy writing or performance?

I have only had two official jobs with a consistent paycheck. One was as a contributor to MSNBC when they first went on the air in 1996. The other was with 60 Minutes II where I was a commentator for two seasons in 1999 and 2000. Other than that, it has always been a series of one-nighters or a week at a comedy club or a month or two at a theater. My first job that paid was probably street performing. My first official paycheck I think was at a gong show or talent contest. Most of the open mike nights gave the performers a free beer.

What is the biggest difficulty you have encountered being a comedy writer?

The biggest difficulty is trying to please everyone — the audience, producer or client, and myself — at the same time.

Are there jokes that you do just for you?

Jokes just for me? Not really. They are all for me; if they don't get laughs I don't do them anymore. There are pieces I do that are not funny but they are important to the story I am telling so I do them. This is only true in theater shows, not clubs or private parties where they are hiring me to be funny.

As a political comedian, what is your biggest challenge?

Biggest challenge as political comedian is to make a point and be funny to people who do not agree with you. It is also a challenge to say something about the issue or individual without resorting to their obvious attributes or flaws — height, weight, hair, dress — but rather something about the policy or political positions they are taking. The greatest thrill is to make people laugh at a point of view on a hot button issue they do not agree with, like immigration or gun control.

How did your schedule work, writing your spot for a weekly TV show?

I did not really have a set schedule. Some bits I wrote that week or day. Others I did were bits I had been doing for years and were tried-and-true pieces that worked great for TV. It was always a challenge to write well and consistently on deadline. That was a muscle I was not really required to use as a stand-up comic, but for weekly TV show it is indispensable.

What do you find exciting about comedy right now?

What's exciting now is all the outlets and a really well-informed public concerning social and political issues.

Where do you think the future of comedy is headed?

I think comedy will continue to improve just like everything else. Ball players are better and faster and smarter than twenty years ago, technology is better. I would say the same will hold true for comedy; it will always reflect where society is at that moment. With all the outlets there will be less filters so more voices will be heard.

As audiences are becoming more specific and more segmented, is that making your job easier or more difficult?

I think with the interest in politics and the proliferation of media outlets it makes my job easier and more mainstream than when I started in 1980.

What is the best thing about being a comedy writer?

The best thing for me is to be able to articulate what I'm feeling most of the time. To be paid for something I love doing. To be able to use the craft to actually effect social change and to help deserving people and causes.

Do you have any advice for up-and-coming comedy writers?

Advice? Do what you love, follow your heart, follow your passion. In 1980 before I had even done an open-mic night in Cambridge I was traveling around Europe with a friend with the Eurail pass. Soon I was out of money and took to street performing for beer money and food. A very kind man amused by the test-tube baby blues bought my friend and me fish and chips and a pint or two. He said something I will ever forget as we said our goodbyes: “Sing your song, lad, sing your song.”