The Simpsons: 10 Guest Stars That Must Appear Before The End
2. Madonna
She's been an icon for decades, so it's actually rather odd that Madonna hasn't been a bigger part of The Simpsons world. The Material Girl was being targeted for a cameo back around 2007 by Simpsons creator Matt Groening, who said at the time that "we would love her to do the show. She’s one of the people we haven’t been able to get yet."
Over ten years later, and we're no closer to seeing Madonna on The Simpsons. Britney Spears has done it, all the way back in 2000 in the episode The Mansion Family, recording her lines when she was just seventeen. Lady Gaga has done the show as well, taking center stage in the season twenty-three finale, Lisa Goes Gaga.
Yet the original pop icon, arguably the biggest name in pop music in history? Nothing yet from The Material Girl. Which is a shame, because a duet with Milhouse singing Like a Virgin would be killer.
We know he has the chops. After all, dad Kirk Van Houten crooned the classic Can I Borrow A Feeling.