For a supposedly unfussy plant,privets are a pain in the neck. We have about 60 feet of privet hedge, so I have an idea of what you're going through.

I think that you have an older, mature hedge, and you are trying to keep it a specific shape which has no room for new growth; therefore, you are cutting off all the new growth and leaving the old framework, but with no glossy leaves. It looks like you have cut back into the bare internal branches in a couple of places. These will all try to grow again, only to be cut off again.

You have a couple of choices. First, let the hedge get a little bigger - don't cut it back quite so far the next time. This will give you new growth for a little while, but then you'll be back to where you are.
Second- cut the whole damned thing down to 8 inches or so and restart the hedge. I have done this twice in the 25 years we've been in this house, and I would gladly have done it more often, but my husband had a fit. Before you faint, let me tell you that I cut back about 30 feet of our hedge down to nubs last fall, and it is now about 30 inches high, fuller, better branched, and green. I have cut the new growth roughly in half twice, to encourage fuller growth. The plan is to let the hedge get to about 3 1/2 feet, and then keep it there, which means that at some point in the next year or so, I'll be cutting off all the new growth too. It's just the nature of privets. Oh, and an additional benefit is that you can really clean out the seedlings, ivy, newspaper wrappers and various stuff that has gotten stuck in the hedge.

Obviously, the downside to the radical pruning is that you lose the privacy the full hedge gives you for a couple of years. Our hedge is more of a boundary marker than a real privacy thing, so we didn't mind too much; your situation may be different. You could do the big cut-down a bit at a time, and spread the full thing out over several years.

If your hedge is as old as it looks, it probably doesn't need to be watered regularly, but you do need to see what the soil is like underneath. If there is a lot of ivy rooted there, the hedge could very well be extremely dry. If there is a maple tree close by, ditto. An asphalt driveway, a concrete driveway - lots of things can affect the state of the soil.

The spots on the leaves could just be some kind of scalding from the sun, or maybe someone was spraying weedkiller or other chemicals nearby and it got blown onto your hedge.

I think you might be right. The Privet is very old and has just been repeatedly cut into the same shape. I do plan on cutting it a little shorter and I have experimented with one bush cutting it to a stump. It is growing back nicely. My only issue is I need the privet wall. I am on a main road and it is my only protection for garbage and for privacy. Last year on the other side of the house They were looking thin and sad. I tried advice I read in a thred on here and when through and cut out a few trunks here and there to thin it out and rejuvinate. That side is looking way better this year and even though I really had to prun it hard to fix the shape it is leafing out and looks good. Even another section that I didn't do that do last year I just trim it as usual looks better. I am going to take the height down more in the next few weeks when I trim again. Maybe I will go a little more so after that some new growth can stay.
Also, I do have a Japanese Maple near some of the Privets, not that close to this stretch of Privet. The privets were planted along a poured concrete trim. It is about 6 inches wide and goes down in the ground over a foot deep. I guess most of the roots go to one side I guess. I can see though that big roots have grown over the concrete into the ground on the other side.

They only take so much butchering and then give up. They are generally plants that grow ~15x15'. If you were beaten down long enough you'd give up too.

Dan

If privets, or most any other hedge plant, is pruned so the top is wider then the bottom that can shade the bottom enough so there is little new growth there. All hedges should be pruned so the top is narrower then the bottom.

Dan-
I wish that it were true. Our privets are, according to old pictures of our house, close to or over 100 years old, and they've been cut back and hacked at for a century and they still get out of control. I think that they would survive a nuclear attack. I am ashamed to say that sometimes I wish for an emerald privet borer.

That's fantastic - they must have been pruned properly for many years. Lucky!

Dan