I'm yet to have SSB appear in my KL :? Maybe he not aware Bart is there yet
i am pretty sure the reason it crashes is that bob pays out cash and you cant collect cash in krustyland.
the programmers probably forgot to set him to pay out tickets in krustyland.
Its a known issue and theres a lot of posts about it.
Here is the main thread:
Issue: Game crashes if you click on Sideshow Bob while in Krustyland:
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