The Simpsons: Who’s Next

I know many of you have given up on watching The Simpsons, so you might have missed a cameo by a fellow Westchesterite this past Sunday. Pleasantville resident Will Shortz was the latest to get transported into Springfield—and he ran a Simpsons-themed crossword puzzle this Sunday as a tie-in.

In the episode, Lisa becomes a crossword fanatic (or “cruciverbalist” for the initiated) and enters a local tournament. Here’s a clip:

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In his “Wordplay” blog, Shortz writes about his experience with the show: “Because of the Hollywood writers’ strike last year, the show was prepared early. The script had me speaking two lines. I taped them Oct. 31, 2007 (just ahead of the strike), at a studio in Manhattan, with the writers and producers connected in California. Despite my very small part, the taping took almost a half-hour, so I could do the lines in different ways, first emphasizing one word, then another, and then another, ‘with more feeling,’ etc. After the strike ended the script was revised, and I was given a third line, which I went back to the studio to do.”

Shortz is just the most recent in a line of ingenious Simpsons cameos. Instead of heading straight for the huge-name stars, they always manage to offbeat, celebrated personalities into the show: Hairspray director John Waters, comics writer Alan Moore, super-genius Stephen Hawking, scientist Stephen Jay Gould, etc. (I had a friend who went to a discussion with Gould, and during the Q&A he was very dismissive of the Simpsons experience, which tarnished his reputation in my opinion.) The crossword guru isn’t the first Westchester personality to be given the yellow-skin treatment, either. I’m pretty sure they’ve done Ron Howard, Bill Clinton, and David Letterman, too. The question is, who should be next? Here are my top five suggestions for future Simpsons cameos.

1. Hillary Clinton. She could be a good role model for Lisa, who was once so passionate about becoming president before her friend Janey that she yelled, “Not Janey! She’ll pack the supreme court full of boys!”

2. Simon Schama. I’d love to see Schama’s take on A History of Springfield.

3. Ralph Lauren. As far as I know, the show’s never really done an episode about the fashion industry. Marge is tall and skinny as a beanpole—couldn’t you just see her on the runway?

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4. Ang Lee. The show has one crazy vision of how Hollywood works—see Ron Howard’s episode, where he was always shown in his bathroom mooching off Alec Baldwin and Kim Basinger—and I’d be interested to see what they’d do with Lee’s difficult an controversial reputation.

5. Martha Stewart. Who would win in a casserole bake-off: Martha or Marge?

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