Tidy up:

gistfile1.py

#I'm looking for a terser way of converting a 2D list into a list of tuples and values -
#perhaps using comprehensions or zip/product/enumerate though without sacrificing readability.
#. For example:
  [
    [ True, True ],
    [ False, False]
  ]
#Becomes:
  [((0, 0), True), ((0, 1), True), ((1, 0), False), ((1, 1), False)

#This is what I have now:

  results = []
  for row_index, row in enumerate(grid):
    for col_index, alive in enumerate(row):
      results.append(((row_index, col_index), alive))

#Possible implementations are:

  [((x, y), grid[x][y]) for x, y in product(range(len(grid)), range(len(grid[0])))]
  [((x, y), alive) for y, alive in enumerate(row), for x, row in enumerate(grid)]

#though these both sacrifice readability for the sake of short code.

#Is there a cleaner way of implementing this?

Personally I'd use your second suggestion (list comprehension with two enumerated loops) as I don't think it reduces readability at all, provided one formats it nicely:

[
    ((x, y), alive)
    for y, alive in enumerate(row)
    for x, row in enumerate(grid)
    ]

That makes it nice and obvious that you're dealing with a nested for-loop. The only difference between this and your original code (which is perfectly readable) is that the portion that defines the output ((x, y), alive) is at the top instead of the bottom - but that's perfectly normal for a list comprehension so I wouldn't regard it as a problem.