The Simpsons: Every Crossover Episode Ranked - From Worst To Best
5. The Prisoner
The "crossover" between The Simpsons and ITV's The Prisoner, which originally aired in the late 1960s, was again more designed more as a parody, but which featured the star of The Prisoner, Patrick McGoohan, voicing the same character he portrayed on the show, Number 6. It also reintroduced the show to an entirely new generation. In that sense, it was more than just your average parody - in going out of their way to get the genuine article, the producers of The Simpsons gave fans of both shows something special.
Appearing in the season twelve episode The Computer Wore Menace Shoes, McGoohan's appearance was a welcome - and rather random - addition to the show's crossover history. Of all the shows to pick, why that one? Who on the Simpsons writing staff was a big fan?
Interestingly, the actor would later be quoted (by his wife, nonetheless) as saying that he was as proud of his appearance on The Simpsons as "anything in his career." That's rather high praise for a very silly crossover appearance.
Towards the end of his life McGoohan was connected to several attempts to revive the show, but sadly, it never worked out. Though the series was brought back as a mini-series in 2010, McGoohan had had no part in it.