Richard Kelly was no good director; just look at the three leads
After all these years I still cannot get my head around why Kelly would cast Sarah Michelle Gellar, Dwayne Johnson and Seann William Scott as the three leads who carry all the secrets to what Kelly saw as his 3-hour long masterpiece of a movie. There is a reason why none of them had huge acting careers (please no confusion here with having a huge movie career, I know that Johnson has been in some highest-grossing movies at the box office for the past years) and there is a reason to it. None of them ever was able to successfully carry a dramatic role successfully, let alone being successful constantly (Gellar and Scott seem to have disappeared almost completely from anything relevant ever since their TV and American Pie successes). Don't get me wrong, they are okay actors, seem like nice people, Johnson seems fun, but no one should ever cast these three in such a heavyweight of a movie; especially not in the roles they were asigned (I mean, gellar as a porn star, come on!).
Yes, I get this is satirical in some ways, yes there are popcultural allusions in there, but with such an inconsistent movie, casting people for the sake of shock or surprise effect simply doesn't do it. Therefore, them getting cast as well as their performances make no sense all the way. And I attribute this all to Kelly and his direction. He wanted to go against typecasting, which is fine, but even going against typecasting has its limits. We all know, Gellar can be sexy, see Cruel Intentions, but Kelly somehow made her not only the blandest porn star of all times but also made her look like a bad actress since she couldn't play dumb and ignorant convincingly. And I cannot get my head around how he directed Johnson as a maniac. He just seems stupid, a rambling idiot, and is not psychic schizophrenic.
Since the trivia states that Timberlake had to re-record all of his lines for the recut-edition since Kelly claimed he misdirected him as too sarcastic, I can only feel that he also misdirected his three lead parts on all levels. A good director gives his actors directors and doesn't let them walk right into a trap