Re: 295/45 20 on Overland original wheels
A little late to the party I know, but...
There are two problems:
1) I agree with the rest that a 295 is too wide for an 8" rim, regardless of the applictaion. Just not safe.
2) When deciding on larger tires I installed a 275 (like a lot of people run) on my 18" WK2 rim and there is no way anything wider will clear on a stock rim, without spacers.