"Back when the security was relaxed, I would slip scripts under producer's doors and occasionally they would buy them," he told North by Northwest's Sheryl MacKay.
Boothby, now the head writer of The Simpsons and Futurama comic books, credits that early sleuthing to his eventual love for writing.
The Shuster award-winner will be attending this years Vancouver Comic Arts Festival which runs through the weekend. The festival brings together cartoonists across the country to share ideas, host panels, and attend workshops.
It was at an alternative press expo years ago where Boothby says he met The Simpsons co-creator, Matt Groening.
"He was one of the reasons why I became a cartoonist. He was not a good artist, but he could get his ideas across with his very simple art."
Boothby now writes the 10 Simpsons and four Futurama comic books released annually. He admits that while the job is one of the best in the industry for a cartoonist, the challenge is to constantly come up with new material.
"The real trick is finding a story that hasn't been done on The Simpsons when they've done a thousand stories already. It really does take a lot out of you."
While his own entry into the comic industry may have been more unorthodox than others, Boothby still has advice for young cartoonists hoping to follow a similar path.
"If anyone wants to do this kind of thing, my advice is to self-produce whatever it is you do. If you want to do films, make your own films. If you want to write, write your own stories. When you do get an opportunity you'll have something to present."
The Vancouver Comic Arts Festival runs from May 23 - 24 at 181 Roundhouse Mews in Vancouver.
To hear more, click the audio labelled: Simpsons comic writer attends VanCaf Festival.