Futurama has long been known as something of an intelligent show.
The futuristic background has given license to the creative staff to reference issues concerning the intersection of math, science and philosophy. In "Free Will Hunting" there is a very interesting question posited:
Does an automaton truly have free will? What is the purpose of a creature who doesn't have a free will? A great science fiction writer could write a profound tale concerning this issue. But this is a comedy starring a drunken felonious robot, so the approach is somewhat different.
Sure, we've seen Bender and other robots take plenty of action seemingly of their own volition, but the show put forth the idea that they're not actually in control of their actions. They're making decisions based on their programming, and they are restricted from doing certain things. So, when Bender says "Kill all humans!" they're just cold, empty words – unless someone ordered him to kill all humans, he wouldn't really do it.
Or, more accurately, he couldn't, as he proved before eventually getting free will installed.
This episode was odd in its structure and tone. There was no B-plot at all, just Bender's quest for free will that started out at full steam from the beginning. Even the first couple minutes, which are usually used as a kind of diversionary set up for the episode's theme, didn't really let up, and the "decisions" motif was immediately apparent.
This focus on just the A-plot shows why having separate stories in programs is necessary: there's just no room for the viewer to breathe when it's just the one story. I think it was necessary for Bender's free will journey to be just the focus of the episode, being a complex topic, but it just caused the whole thing to feel somewhat odd on the first watch. I didn't find myself noting as much funny dialog either. The humor came more from the goofy scenario presented rather than from characters saying a lot of funny things.
Where I think the whole affair fumbled was in the end. Professor Farnsworth seems to give Bender the free will unit for no good reason, and there was almost a point made about how perhaps if we did or did not have free will, there would be no way of knowing due to the quantum nature of the device. Yet, they decided to go for humor, with Bender utilizing free will to shoot Professor Farnsworth. I think it would have been a better fit to have an ending open to interpretation to really play off of the philosophical issues that were raised.
Still, this feels difficult to critically judge. I was captivated, but not entirely satisfied. I wouldn't describe it as risky, but I do think that it was thoughtful, yet flawed in execution.