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Some Sportsters came with a 150 -80 x16 rear tire. It's a Dunlop d401. It is designed to fit on a three and a quarter inch wide rim which is basically what the factory rear Rim is. Your issue is going to be the sidewall of the tire clearing the wider belt that comes on a 2001 versus the narrower belt that came out in 2004. The other thing you're going to run into is clearance of the sidewall at the rear fender strut. Different tire widths and sizes and Brands can all determine at a plus or minus 7% size variants what will or will not fit. Sometimes it's hit or miss. Changing to a chain drive will give you room. I've dome that...
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Dont know. I can assume. for reference:

My rear fender is 8.25" wide between rails and 7.25" at top width.

My belt is just shy of 1.25" wide. I have the newer style pulley. not the old one with circles in it.
 
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