Will a 295/55r15 tire fit a 81' monte carlo? Just wondering, I'm planning to get some M/T ET Street S/S and a pair of 15x8 wheels.

I don't know if it fits or not, I would consider a 10" wheel for that so that it doesn't roll the tread corners up off the ground.
 
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A 295 is too much tire for an 8" wide wheel. Will that tire fit on a 15x8? Sure, but it's intended for a wider width rim. The sidewalls will be pinched vs square to the rims width.

A 255/60 is slightly shorter (27" vs 27.7) & the 255mm section width is better suited for the 8" rim width.
 
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For what it’s worth I had 275s on an 8 inch wheel on the back of my 81 Malibu and had to use spacers to get them off the frame. That was on a 4 1/2 inch backspace 8 inch weld wheel
 
For what it’s worth I had 275s on an 8 inch wheel on the back of my 81 Malibu and had to use spacers to get them off the frame. That was on a 4 1/2 inch backspace 8 inch weld wheel
255's under my Malibu. 15x8 w/4.25"BS & no spacer.
 
255's under my Malibu. 15x8 w/4.25"BS & no spacer.
I had 255s on the same welds and all was good, no spacers. The 275s were just too much with that backspace.

Now running 245/45-17 on 17x8, 4.5 backspace and very happy with it
 
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I have 295/55R15 MT Drag Radials on the rear of my Monte on 9.5" rims and I did a frame notch to give me the needed clearance.

IMG_0015.jpg
 
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You have to do a lot of work but I have 295/50/15 on 15x10's all the way around and they don't rub. Lol
 

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