In 1962, future Pulitzer Prize–winning author Alex Haley sat down with jazz musician Miles Davis for what would become an institution of American journalism—the Playboy Interview. To celebrate the Interview’s 50th anniversary, Playboy has culled 50 of its most (in)famous Interviews and will publish them over the course of 50 weekdays (from September 4, 2012 to November 12, 2012) via Amazon’s Kindle Direct platform. Here, a glimpse at our conversation with cartoonist and Simpsons creator Matt Groening from the June 2007 issue.

“In general The Simpsons is among the most bootlegged creative properties in the world. I find it much more amusing than the Fox lawyers do. If some bakery does a Bart Simpson birthday cake, Fox wants its cut. There’s a Russian Simpsons coloring book that looks as though the guy who drew it was shown a picture of The Simpsons for five seconds, was never able to look at it again and dropped it from his memory. I had a large collection of Bart Sanchez ceramic figurines from Tijuana, but I lost dozens of them in the earthquake. Priceless, priceless treasures—gone. I have Bart yarmulkes from Israel and from Italy little glass Bart figurines peeing.”

“We have turned a few things down, believe it or not. I know it’s hard to tell. We turned down Simpsons slot machines in Vegas because we thought, You know, you have to draw the line somewhere.”

“I appalled some of my friends with how undisciplined I was as a parent. My kids talked back to me, and I laughed it off. Now they tell me I’m not funny anymore. I just assume they’re kidding. My son said he wishes Seth MacFarlane were his father. So I annoy the hell out of other parents. I’m a really bad example. I’m the dad I wished I had. I try to let my kids have a good time.”

“My friends and I used to sit around when we had so little money that we had to split a burger at Astro Burger on Melrose Avenue and talk about what we would do if we ever had enough money to pay our rent on time. We wondered if we would live the way rich people were supposed to live or if we would live pretty much as we did then, except that we would have bigger piles of comic books and toys. Sadly, we’ve got bigger piles of comic books and toys.”

To read the interview in its entirety on your Kindle App, Kindle Fire or Kindle Touch, click below.

*Or read the interview with access to all Playboy interviews on iPlayboy.*