Bill Hicks was the type of comedian who mixed extended philosophical musings in with his more straight forward comedy bits. Sometimes the serious part of his act would go on so long that he would have to stop to reassure the audience that he hadn't forgotten that he was putting on a comedy show. Specifically, he would say that while it might seem like he was lost at sea he had never lost sight of "Dick Island" and he was going to return to it's fabled shores soon enough.
I really like the phrase "Dick Island". To me, it conjures up a specific ratio of frivolity to reality: it's an oasis we retreat to when the cold, undrinkable, full-of-sharks water of life gets to be a bit overwhelming. Comedy shows almost always take place in some version of "Dick Island", but comedians rarely reference the ocean around them, because acknowledging the darkness that's just out of sight makes it harder to make the audience laugh. But occasionally, you'll get somebody like Hicks who is trying to see how far they can get away from Dick Island before they are lost at sea. Monty Python tried to do that with "Always Look on the Bright Side of Life", it's optimistic take on crucifixion. When The Daily Show stops kicking easy targets like Fox and Friends and really engages with the news, it does that.
The Dictator really wants to do that. The Dictator is a political satire about a brutal and dumb dictator named Aladeen who comes to New York to deliver a speech at the U.N. about his chemical weapons program. While he's there his closest adviser stages a coup and switches Aladeen with his assassin distracting body double, an even dumber goat herder. The real Aladeen has five days to get back into his rightful spot or else the adviser is going to permanently dismantle his throne and sell all of the country's oil rights to international corporations.
The movie is designed to skewer a lot of targets: the absurd egotism of Middle East dictators; the average American's willful ignorance of foreign policy; the well meaning but misguided empathy of super liberal co-op members. But most of those jokes tend to have a hard edge to them - for example, jokes about rape rooms and ironic racist comments abound. Those jokes might be well informed, and they might be funny, but they are also deeply misanthropic, since they focus on how much hate there is in the world.
Periodically the movie will pull back from it's political satire for a more conventional kind of skit. The scene where Aladeen 'helps' a pregnant woman give birth in a grocery store and ends up losing his cell phone inside her vagina doesn't have any real sociopolitical point; it was clearly put there because it was a purely comic scene that could keep the movie's tone from becoming too political or too bitter. That skit (which is probably the funniest part of the whole movie) is the Dictator's attempt to get back to Dick Island after swimming against the harsh current for a bit too long.
If the Dictator had managed to balance those two tones evenly it could have been a great movie. Unfortunately that mixture of absurd skits and dark humor doesn't actually gel that well, because the pointed nature of the satirical bits makes them feel very different from the apolitical bits which are far more silly. The sort of dictators who have rape rooms are a ripe enough target for parody (as South Park well knows), but it feels schizophrenic to establish Aladeen as that sort of monster and then put him through the paces of a traditionally plotted romantic comedy.
If this movie had wanted to really commit to being a dark satire of Middle Eastern politics, it might have been too harsh for a mass audience, but it could have been quite good; Four Lions did that and I found that film to be wickedly funny. Or if the Dictator had been a thoroughly silly comedy about a prince who falls in love with an unlikely American, it could have been pleasantly funny, like Coming to America was. Instead, it didn't want to commit to being one or the other, and it didn't even want to start as one and grow into the other - it wanted to throw the two tones together willy-nilly, and that doesn't really work. It takes a sure hand to steer a boat in the choppy waters around Dick Island, and while Aladeen might have that level of decisiveness, the Dictator definitely doesn't.