I think Futurama is far cleverer and more nihilistic/dark than The Simpsons. Then again, Simpsons was a syndicated Fox affair, so the "family friendly" element was pretty forced. Now it's in like its 20th fucking season, and it's absolutely terrible. Simpsons stopped being funny or likable somewhere around 2002-2003, and that's being generous.
Futurama has only ever made me lol on a few occasions. It's humor is the kind of droll irreverence at which you smirk snidely, not necessarily laugh out loud. Actually, the lines that made me laugh the hardest were the real derpy ones. One that comes to mind is...
Bender: 'I'm a big robot and I want a big cereal!'
Fry: 'You too!?'
This line actually became less funny when I learned it was a reference to the classic Honeycomb commercials. It was so juvenile in it's structure and delivery, and it came so far out of left field that I did a double-take with enough swiftness to give myself testicular torsion.
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