The Kaufman connection could mean we should expect Alex Trebek to show up as himself in a surreal sort of comedy akin to Being John Malkovich. Or, Trebek could be more similar to Confessions of a Dangerous Mind, which also went behind the scenes of a game show in its biographical portrait of The Dating Game
I also must admit I'm looking forward to Maguire doing something relatively unconventional. I've grown pretty tired of him in the Spider-Man movies and haven't really bought him in anything else since 2000's Wonder Boys. He's a pretty awkward actor, and he can't do the leading man stuff any more than he can be a non-costumed action star. He's fine in some serious dramas but he belongs in more quirky and fantastical fare, even if only as out there as Pleasantville. If you've seen him do SNL or in Fear and Loathing in Las Vegas you know he can be more comical. Hopefully Trebek will allow him to loosen up a bit, maybe wear a silly wig.
Meanwhile, there's another report that Maguire is potentially headed for something very mainstream and fantastical: The Hobbit. Apparently the actor recently revealed in a junket that he might soon be working with Guillermo Del Toro. So Latino Review went and confirmed with their sources that CAA is talking to producers of The Hobbit about casting Maguire in the lead, as Bilbo Baggins. Despite his continued involvement in the Spidey series, it would be nice to see him take on another franchise, but can you picture Maguire with the furry feat and what not? Nothing is set in stone on this, so we'll just have to wait and see if it's a good idea.