I like that lambda trick. I was hoping Crash would actually crash the program so you could tell if you won by looking at the error it gives (if its KeyboardInterrupt or something else).

Here's mine.

  $ python -c 'import random;L=sorted(str(random.randint(1,9)) for i in range(4));a=raw_input(L);print(eval(a)==24,sorted(filter(str.isdigit,a))==L)'
  ['2', '6', '7', '8']8*(7+2-6)
  (True, True)

Try to make it print (True, True) without abusing eval too much (intended to be +-*/() only with digits as tokens).

A nicer interface, but too long:

  import random;L=sorted(str(random.randint(1,9)) for i in range(4));a=raw_input(" ".join(L)+"\n> ");print(eval(a)==24,sorted(filter(str.isdigit,a))==L)

For some reason copy-pasting some of those into iTerm2 doesn't work.

http://i.imgur.com/GEMAeM8.png

These are pretty neat and very concise! :D