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That time Jack Black starred in The Simpsons and tried to do a Bond gag.

One thing that’s great about animated comedies is the ability for many of those shows to rope in some notable guest stars. Doing voice work doesn’t require the same commitment to set, makeup and wardrobe a regular TV appearance might and doing voices stints can be pretty quick and painless.Thanks to Fox’s The Simpsons being animated, critically acclaimed and on for a large number of years, the show has seen numerous awesome guest stars appear, including the likes of Jack Black. Unfortunately, due to the bent of the episode and the people behind James Bond, “painless” is probably not the term I’d use for this particular role.

The nice thing about getting a bunch of Simpsons people together for an event is they tend to like to reminisce. At this summer’s Comic-Con at home event, those related to the long-running show reminisced about some of their favorite guest stars, with writer and producer Matt Selman telling just a wild story involving the Korean language, Jack Black and the powers that be behind the wildly successful 007 franchise.

We had Jack Black, who has a special place in my heart because he had to sing in Korean, phonetically learn in Korean the song ‘Goldfinger’ and the James Bond people wouldn’t let us use ‘Goldfinger.’ [We’re like], ‘Once we send the James Bond people the video of animation, they’ll see how funny it is.’ No, they wouldn’t clear it. So he re-came in and sang ‘What’s New Pussycat?’ in Korean. He really was a pro. Then, we could never force him to come back and do the character again.

Jack Black popped up in this episode of The Simpsons all the way back in 2007 – and he hasn’t been back since, though it sounds like he was really professional despite all the brouhaha. Honestly, the whole gig sounds like a nightmare, even if it all turned out OK in the end. As Matt Selman noted in his story, Black's character Milo in “Husbands & Knives” (which sounds like the title of an ID series) ends up singing “What’s New Pussycat?” in Korean. It’s a pretty successful plotline and on brand with the sort of comedy Jack Black likes. But it took a lot of work to make this happen:

Again, that's Jack Black singing. In Korean. All of the work Jack Black had to put into "Goldfinger" only to be told “no” by an outside source must have been crushing. Now that it’s out there that the episode could have featured the same gag with the Bond track, it’s also annoying as a fan of both franchises to think about what could have been.

Then again, around 2007, Bond was just starting to take itself pretty seriously. Casino Royale, introducing Daniel Craig as a newer, more serious Bond, had just come out a year earlier. I have no idea if that was the problem for the Sony/MGM people at the time or if there were some rights complications involved, but as Matt Selman noted, they refused to clear it and Jack Black had to learn to sing a second song in Korean. Remember when I said voicing animated characters is usually pretty painless?

Meanwhile, some of the other staff involved talked about their favorite guest stars on The Simpsons, albeit in less detail. Both showrunner Al Jean and writer Carolyn Omine had some fun picks, as well.

AL JEAN: Too many to name because they’re all wonderful, but for me I’d say, Lovitz, Kelsey, Anne Hathaway. All great and clearly talented.

CAROLYN OMINE: I love – Cate Blanchett was great. When Sacha Baron Cohen came he was so funny. He came in with like three different ideas for his character, the voice. When Don Cheadle came in, he actually came in with music for the [episode]. He said, ‘I dunno if you guys have already written music for this,’ and he had it. There’s been so many great people.

If you are already pumped about the new season of The Simpsons on Fox, Al Jean also did mention some of the stars who will be a part of Season 32, which is set to debut on Fox this fall. Amongst those guest stars will be “Hannibal Burress, Olivia Coleman, David Harbour from Stranger Things and Ben Platt.” Meanwhile, the fall TV schedule is still shaping up given current world events; however, you can take a look at what is locked in with our full schedule.

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