Whatever urllib is using to figure out Content-Length seems to get confused by json, so you have to calculate that yourself.
import json
import urllib2
data = json.dumps([1, 2, 3])
clen = len(data)
req = urllib2.Request(url, data, {'Content-Type': 'application/json', 'Content-Length': clen})
f = urllib2.urlopen(req)
response = f.read()
f.close()
Took me for ever to figure this out, so I hope it helps someone else.