Lukas Lueg added the comment:
The behavior is triggered in Modules/_json.c:encoder_listencode_obj(). It
actually has nothing to do with the TypeError itself, any object that produces
a new string representation of itself will do.
The function encoder_listencode_obj() calls the user-supplied function with the
instance to get a string, float, integer or whatever it knows to how convert to
json by itself. As the function keeps returning new instances of TypeError, the
recursion builds up. The MemoryError is ultimately triggered by the fact that
repr() keeps escaping all single quotes from the previous repr(), generating a
huge string. Also see "repr(repr(repr("'")))"
Testing with 2gb of ram and no swap (disable to to prevent starvation instead
of immediate crash!), cpython dies within 34 recursion levels. The
obj-parameter for encoder_listencode_obj() looks like "Foo(obj='<Foo \'<Foo
\\\'<Foo \\\\\\\'<Foo "<Foo \\\\\\\\\\\\\\\'<object object at
0x7ffff7f52100>\\\\\\\\\\\\\\\'>">\\\\\\\'>\\\'>\'>')".
My two cents: This is expected behavior. The json-module has no way to tell in
advance if the encoding-function never returns. The fact that repr() causes
this blowup here can't be fixed.
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nosy: +ebfe
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<http://bugs.python.org/issue21213>
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