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I find Se7en an amazingly good movie, but among its weaknesses is the Envy killing. I found the justification for it very unconvincing, as if forced into the story, just so we can have the (iconic) something-in-box scene. Not being a psychologist, John Doe doesn't strike me as a guy who would get jealous, especially for something so petty. Is there something I'm missing?

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Not sure how an isolated, mentally challenged, psychotic can't envy the life of a simple man?

Often geniuses become insane and often wish they were more simple. The saying "ignorrance is bliss" definitely came from somewhere.

So what would be wrong with John Doe envying the life of a simple family man? I thought it was brilliant.

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Like this answer suggests, I think Doe was envious of Mills' family life, which Doe recognizes he could never have for himself – Shane Finneran Mar 5 '12 at 2:51
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There is another weakness. After all the well-planned murders to prove his point, he involves for the last two people, who recently moved in the city: Mills and his wife. Doe couldn't possibly have known about this.

I have two theories explaining this. First: Doe got under pressure after the police caught his trace. He had to switch plans, so the last killings were planned under pressure and not perfect. Second theory: He always planned the wrath involving the policeman going after him. He planned that after the first murders some detective will catch his trace. But to enrage him, he needed to hurt him really bad. So he planned to use the wife of whatever detective it will be. To match the scheme it had to be the Envy-murder, but as it had to be improvised. So it lacks the perfection he tries to achieve.

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So you are implying that John Doe was dishonest (he wasn't envious)? I have considered that possibility, but who knows if that's what the writer intended. If so, he is truly masterful. – Tshepang Dec 10 '11 at 6:26
I don't think Doe was dishonest, but you are right, it misses a little credibility (so you're also implying dishonesty). I got the feeling Doe tries to achieve perfection in this murders. In many cases there is no doubt about the sin. In the case of Envy, we have to believe him he was envious. While it is believable, it misses the perfection. I think that's because it's partly improvised. If he had more time to think it through, he would have come up with more hints to his Enviousness. – Mnementh Dec 10 '11 at 8:01
Just to be clear, if the writer intended for Doe to be dishonest, the writer is remarkable (and I go with both your theories), but if not, that's when the credibility crumbles. Anyways, what do you mean he misses perfection, assuming he was honest about the Envy murder? – Tshepang Dec 11 '11 at 6:31
First, I think he is honest. Doe wanted perfection in his murders, as he wanted to show society their sins (I think he said also, that it is an work of art, but my memory may trick me in this). But in the other murders it is clear, which sin is meant and why. With envy it is not that clear. That's why you ask about the credibility. I can believe him, that he is envious, but believe wasn't so much needed for the other cases. And I think the perfection misses, because he hadn't enough time to give better hints. But it could also be imperfection on the side of the writer. :-) – Mnementh Dec 11 '11 at 23:12
remember that John Doe made contact with Mills at one of the crime scenes, when Doe was there taking pictures. I always thought Doe keyed on Mills after this meeting. – Shane Finneran Mar 5 '12 at 2:49

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