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I find it amusing that any parent would think they can stop their 16 year old from finding pornography on the Internet. I also wonder what these parents think will happen when their 16 year old son does find pornography on the Internet.

I'm so thrilled to hear that you spent a lot of time with OS X's parental controls. I'm hoping you spent enough time to discover how fatally broken they are. At first glance they seem great -- until you discover that your kid was never forced off when they were supposed to be, or websites just won't work at all for mysterious reasons even if they're in the white list, or any of a number of other issues. This should be Apple's biggest black eye at the moment, but for some reason it's not and because of that Apple doesn't seem interested in ever fixing the issues.

One workaround you could have suggested is to enable router filtering, e.g. MAC address filtering, web filtering, time of day limits. Not every router comes with the more robust filtering features but they all have MAC address filtering. This wouldn't solve the problem of using Safari outside of the home, but it would prevent the boy from surfing from his bedroom. (And yes, I know MAC filtering is fairly easily circumvented, but it's at least another hurdle).
Alternately, the parent could just not give the child the wireless password.

There is a simple solution to all of this:
Move to the middle of Africa.
Well, not simple actually.
I'm aware of several kids who have been raised in highly 'conservative'/religious homes with the kids being very contrite in character, yet found out how to exploit technology "just to prove" they could.
When parents asked me what to do, I simply noted that the iPhone / touch is a material want, not a religious need.
We feed our children with gadgets galore, and then want to reign them in hard when we're headed full-bore for the cliff.
WHy don't my kids go to R-rated movies? Not because I restrict them not to, I taught them early on in life how to discern good from bad.
You've heard of the "Terrible 2's", referring to temper-tantrum toddlers. The implied reference is incorrect. It's not the 2-year old toddler that is 'Terrible', it is the two parents for not teaching their child from the get go (birth).

I wanted to point out something that's not immediately obvious with the iPhone/Touch parental controls. They're locked with a 4 digit number. So you might think, "4 digits? Hah! My teen will figure that out in less than an hour!" That's what I thought and that's the reason we initially denied purchase of a Touch.
But then I experimented on my Touch. After 6 "guesses" I was locked out from entering the code for 1 minute. After the 7th guess I was locked out for 5 minutes. After the 8th guess I was locked out for 15 mintues. After the 9th guess I was locked out for 60 minutes. I can only assume it goes up from there, because I wanted to turn my Safari access back on after that!
So I initially thought 4 digits was dumb, but now I think it was a really smart implementation. I couldn't find any information on the internet about this, so I thought someone here might find it useful. Or maybe Chris can drop that in his article also. :-)

It is not always about The Porn. Some parents wish to limit a child's internet activity in the same way that parents limit TV, car, cellphone, and junkfood.
I am sure some are thinking "but he is 16!", well, kids are different. J.S. is doing what I think any good parent ought to do, research the options available to make an informed decision. The statement "I don’t know if I want him to ..." means to me 'I am thinking about it, but have not made a final decision.'
I second the recommendation to moderate and control household internet usage through the router.
good luck!

Wow it seems futile to rely solely on Parental Controls anymore. Seems like you need to get a free account at OpenDNS.com (http://www.opendns.com/) and there you can limit whole categories (with a free account settings) with putting no obvious software restrictions on the device. IMHO this is the best way to limit teenagers because they have a HARD time figuring out DNS restrictions.

Like Steve Jobs said, "It's a cat and mouse game." That's just the way it is. If the kid wants to get through bad enough, he will. And how far are we going to push Companies like apple and everyone else to aid in our parenting skills by saying that they need to make parental controls better. They don't need to do anything as far as I'm concerned. What ever happened to the parent being the parent.

Don't be obtuse, guyncall2. These are simply tools the parent can use to do their job. They don't take the place of parenting, and they don't suddenly make bad parents good. But they are extremely useful for parents who want to put them to use as another tool in the arsenal all parents have. And if companies like Apple are going to provide the tools, they should at least work as advertised, and at the moment Apple's simply don't. They're broken and need to be fixed. 90% of the complaints I've seen are not that the tools don't do enough, it's just that they're very buggy.

For this to work properly the parent needs to be an informed-parent who takes things to the core and set things up for the rest of the household. It is intended for a Dad/Mom (adult) to setup the iPhone/iPod Touch so that it can only do certain things when someone else is using.
If the parents enable restrictions on their iPhone/iPod Touch with an appropriate passcode then the kid has to take a guessing-game to try to break that. Guessing a 4 digit code might not be as difficult as it might sound but if done properly this can keep most of the kids parental controlled.
Given the age of this article I would like to point you to a more recent article "Restrict iPhone usage with iPhone Parental Control Restrictions" at DemoGeek.com that is based on the 3.0 software.