Even if film makers can avoid all of the pitfalls mentioned above, there's one problem that's almost guaranteed to sink a prequel before it even sets sail. It's called suspense, or rather the lack thereof. The vast majority of movies that get prequels are action films, a genre that's driven by the conceit that death is around every corner.
No matter HOW cool your costume looks.
A prequel crushes this tension right from the get go. In Star Wars Episodes I through III we know that Anakin, Yoda, Obi-Wan, Palpatine, R2-D2 and C-3PO all have to be alive at the end. Same thing goes for Wolverine, Cyclops, Sabertooth and Stryker in Origins.
But you don't need it to be a movie with sword fights for a prequel to suck. Once the question of "Where's this going? Is this character going to make it?" has been eliminated, the question at the back of our mind becomes "How are we going to get there? Is it going to live up to the vague versions of events I've already supplied in my mind?" Instead of getting swallowed up by the film, the audience is passively judging it. It's the same reason people who have read the book always say they liked it better. The version you had in your head was made specifically for you by your brain. Instead of getting involved in the story, you're sitting back judging how the movie version is different from the choices you made.
We would have given Hannibal a 'fro.
This is probably what tricks us into thinking that prequels are easy to make. We're seeing someone tell a story that we've already told ourselves. This leads us to believe that telling the story our way would have been better. And it would have been. For you. But the rest of the audience would hate your answers just as much as you hated George Lucas'.
Of course, it can't be impossible to make a good prequel. Right? Cinephiles generally point to two films for proof that the concept can work. The first one is Indiana Jones and the Temple of Doom. Wait, you didn't know it was a prequel? That's because the only signal that we've gone back in time to before the events of Raiders is the title card at the beginning that mentions that it takes place in 1935 (Raiders took place in 1936).
In fact, according to Lucas and Spielberg, the only reason it took place before Raiders was because Lucas didn't want the Nazis to be the villains again. If he set the film after Raiders, it would have to have taken place during WWII. They just made another movie with the same central character and called it a prequel so Indiana Jones would be remembered as an adventurer instead of that guy who fights Nazis with a bullwhip. It was a prequel in as much as an episode of Seinfeld from Season 4 was a prequel to an episode from Season 5.
Of course, there's no way to discredit Godfather Part II which, according to prequel defenders, invented and perfected the idea of the movie prequel at the same time by showing how Vito Corleone rose to power.
And provided fodder for this comedy classic.
Except the second Godfather was even less of a prequel than Temple of Doom. Almost exactly one hour, or way less than a third, of the movie takes place in the past. Michael Bay puts more of his movies in slow motion. The idea of setting so many scenes in the past worked brilliantly alongside the story that was unfolding in the present, just like it did in Lost when it was called a flashback.
This was back before his wine years.
Hollywood seized on the flashback part, and over thirty terrible prequels later, they still haven't learned what Coppola knew when he "invented" the convention. And unless Hollywood starts hating money, Ridley Scott's upcoming Alien prequel isn't going to slow the onslaught. We'll all probably go see it, even though we know we'll be disappointed. At least now we'll all know why.
As long as they go over Hicks' past as a college Foosball champion.
Be sure to check out The Truth About The Epic Beard Man Viral Video and The TIE Fighter Pilot Who Saved The Day in 'Star Wars'.