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Can you not use functools.cmp_to_key() for this?
Here's an example:
>>> import bisect, functools
>>> l = [('f', 5), ('d', 3), ('c', 2), ('b', 1), ('a', 0)]
>>> def cmp(a, b):
... if a > b: return -1
... if a < b: return 1
... return 0
... 
>>> bisect.bisect(l, ('e', 4), key=functools.cmp_to_key(cmp))
1
>>> l
[('f', 5), ('d', 3), ('c', 2), ('b', 1), ('a', 0)]
>>> bisect.insort(l, ('e', 4), key=functools.cmp_to_key(cmp))
>>> l
[('f', 5), ('e', 4), ('d', 3), ('c', 2), ('b', 1), ('a', 0)]