I guess this is one thats tough to help with?

I think you'll get responses on the shrub forum.

Hi
I just finished a big job pruning a client's long, very overgrown privet hedge. It borders two properties, and each owner had pruned it differently over the years, and one side had fared far worse than the other, resulting in huge bare stems with all the green at the top. Needless, to say, it was a LOT of work. The other posters have given very good advice--overgrown privets can be restored, but

it takes a couple of restoration prunings spaced months apart over a year.

I myself prune using hand pruners, and don't shear with power tools because I like a softer look. Shearing tends to keep all the green leaves on the very perimeter of the plant, so that most of it is bare wood. Hand pruning gives you more control to prune and open up the inside of the bush to sunlight which really stimulates growth.

I agree that the best time to prune privet severely is during its dormant stage in the early spring, when you should also add an organic shrub fertilizer. But you can do a less severe pruning during the growing season, removing the oldest canes close to ground level, and then cutting away heavy top growth to get light into the interior of the shrub. Privet is tough. I try to shape it so that the shrub narrows toward the top, but when you're dealing with an extremely overgrown bush with little greenery on the bottom half, it ain't going to look great for awhile!

A couple suggestions: Watch the "This Old House" video on YouTube about pruning an overgrown privet hedge. Roger the host gives a good tutorial, but realize that the episode telescopes the labor involved! Second, use a tarp to stack the cut branches on. This makes clean up a lot easier. Third, use a Weed Wrench to pull out any maple saplings that have sprouted amid the privet roots. Also, I found a nearby arborist who came with his truck and chipped and hauled away all the tons of cut branches for $100. It would have taken hours and hours to bundle or bag this material otherwise. Good luck!

Good advice, I was going to suggest progressive pruning over a period of at least a year also but am not sure how capriow pictures the end result.

I disagree with something at the end though. That chipped material is a valuable resource which could have been used to mulch under the shrubs or in a flower bed, cooling the roots, suppressing weeds, retaining moisture levels, adding nutrients and tilth to the soil as it decomposes.

Capriow, dead branches should always be removed. Is your goal for the foliage to begin at ground level, or do you like to be able to see trunks at the bottom?