From the documentation https://docs.python.org/2/reference/datamodel.html#object.nonzero:
object.__nonzero__(self)
Called to implement truth value testing and the built-in operation bool(); should return False or True, or their integer equivalents 0 or 1. When this method is not defined, __len__() is called, if it is defined, and the object is considered true if its result is nonzero. If a class defines neither __len__() nor __nonzero__(), all its instances are considered true.
And for Python 3 https://docs.python.org/3.7/reference/datamodel.html#object.nonzero:
object.__bool__(self)
Called to implement truth value testing and the built-in operation bool(); should return False or True. When this method is not defined, __len__() is called, if it is defined, and the object is considered true if its result is nonzero. If a class defines neither __len__() nor __bool__(), all its instances are considered true.
Try:
class MyList(list):
    def __bool__(self):
        return True
print(bool(list([])))
if list([]):
    print('This does not print')
print(bool(MyList([])))
if MyList([]):
    print('This prints')