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On a longbed it will go up fairly easily. On a shortbed it is a lot tighter. My 285 spare is MAYBE 25% tread left and it is wedged up into the frame rails pretty hard. Mine is also on a 6. 5" wheel so it is a tad taller than most 285's on an 8" wheel. You may need to loosen the exhuast clamps and rotate the tailpipe to make a little extra room but it should fit.
Yep, just BARELY. I have a new 285-75R 16 Walmart Liberator spare. That is the absolutely largest size you will fit in there. I had to experiement while I was at Walmart but it does fit.