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>And there's probably a lot of fun, harmless things to bet on. eg. "Will Conan lead an extravagent musical number at the Emmys?"

I cannot fathom what could be fun about that.

Fun to lose to insiders on the production team?
I don't know why you'd ever put money into something like that. Anyone working on the show will know the answer
Kinda legal insider trading, I guess.
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I mean, what's fun about my specific example? Guaranteed money.
By that definition all terrible aspects of the concept are the same as the fun.
Conan hosted the Oscars.