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Given that we typically need at least 4 bytes just for the PyObject * pointer for each item in a list, I guess real lists are safe.
But how about list-like objects, implementing __len__ and __getitem__? The following appears to run forever on my machine:
class SquaresList(object):
 def __init__(self, length):
 self._length = length
 def __len__(self):
 return self._length
 def __getitem__(self, index):
 if not 0 <= index <= self._length:
 raise IndexError
 return index**2
import bisect, sys
squareslist = SquaresList(sys.maxsize)
print bisect.bisect(squareslist, (sys.maxsize - 3)**2)