Put test.jpg in same folder as script. Written for python 2.x. Written for linux so you may need to remove first line of code. Must have PIL library installed.

rotation_losses.py

#! /usr/bin/python
import Image
	
#Created by vvdr12
#No rights reserved :)
#Have fun and do what you will with it.
		
#_______________________________________________________source
source = Image.open("test.jpg")
img = source.load()
print source.format
print source.size
print source.mode
x = source.size[0]
y = source.size[1]

#_______________________________________________________run
rotation=int(raw_input("\nRotation steps in degrees: (10 is always a safe bet)\n>>>"))
num_rotation=int(raw_input("\nNumber of full rotations: (10 is nice, but may take long)\n>>>"))
end=(360/rotation)*num_rotation
print end
j=0
l1=1
while l1==1:
	if j%10==0:
		print j, "/", end
	source=source.rotate(rotation)
	img = source.load()
	j=j+1
	if j==end:#test .. is usually if j==y:
		l1=0

#_______________________________________________________save
source.save("rotation_losses.png")