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OP - this is roll roofing - not flamed down with tar and laid with a roller, so the look will be similar to what you show. Also, heat from the sun can expand the product after it's rolled out. Many times, the lengths are cut and laid out to soften in the sun and then folded in halves, lengthwise (similar to "booking" wallpaper), a few times and dragged to the final location unfolded and nailed down. That can give you a smoother lay - but either is okay.

Inserting, troweling, injecting tar in the humps and then nailing those locations will only move the hump to another spot - you'll just be chasing ripples all afternoon.

You're going to be putting shingles (or tiles) over it judging from the pictures (from the top down? Maybe you're doing a repair?) - so, once those are on you won't lose any style points from the street view!
 
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