I would put Guybrush Threepwood into any other universe just to see what happens. Make it the Mass Effect universe. The overwhelming tech of the Reapers Vs the reality warping, supernatural level of blind luck that Guybrush posseses. I would love to see how that would end up.
Also I know they are similer but I would put Gandalf in the Harry Potter universe just at the end of book 5. While Dumbledore is sat on his arse NOT teaching the all important chosen one anything remotly usefull about magic, Gandalf would be out getting shit done. I imagine it would go something like this:
Dumbledore: 'Harry it has been 15 years, Voldemort has returned and I have not prepared you in any way so I think now is the perfect time to tell you some important stuff'
Gandalf walks in: 'No worries Dumbledore I sorted it out.'
Dumbledore: 'What do you mean!?'
Gandalf: 'It's sorted. Took the fucker down. Took about a week. You see I didn't spend the last 15 years sitting on my arse doing fuck all'
Harry: 'BURN!'
Also I know they are similer but I would put Gandalf in the Harry Potter universe just at the end of book 5. While Dumbledore is sat on his arse NOT teaching the all important chosen one anything remotly usefull about magic, Gandalf would be out getting shit done. I imagine it would go something like this:
Dumbledore: 'Harry it has been 15 years, Voldemort has returned and I have not prepared you in any way so I think now is the perfect time to tell you some important stuff'
Gandalf walks in: 'No worries Dumbledore I sorted it out.'
Dumbledore: 'What do you mean!?'
Gandalf: 'It's sorted. Took the fucker down. Took about a week. You see I didn't spend the last 15 years sitting on my arse doing fuck all'
Harry: 'BURN!'