Do you have a photo of the location?
is it sunny shady wet dry?

The pine is nice. Run a pipe across at desired height and tie new growth onto that. Or make a lath-like network of pipes to produce a broader surface of foliage. The pine tends to grow as an elevated dome anyway so maybe with that you really wouldn't have to do anything - if your specimen(s) grew or were trained up high enough before arching over to one side. Many older ones around here are fairly tall, well above human head height anyway. For example, although A.L. Jacobson, Trees of Seattle - Second Edition (2006) describes it as "A gracefully floppy semi-dwarf mound" he then goes on to give locations of examples 26' (two of them), 15 1/2', 22', 22 1/2' and 13' tall.

i second a pix request ...

i have juniper horizontalis .. naturally growing down a wall.. facing north ...

ken

We bought this land last summer and haven't cleared the ravine yet. It's so full of shrubs, saplings and poison ivy that you can't see the bottom or even how the slope runs unless you wade through it. Ergo, a picture doesn't show what's there. The intent is to clear and plant it next spring a section at a time. When it's opened up, it would be nice to 'soften' the fence and screen the neighbor's portion of ravine.

Bboy, would the pipe get too hot for the pine? I've used rebar to stake plants but have always slipped a PVC pipe over the rebar to protect the plant. I was thinking about having the tree follow the top of the fence going down but using a pipe across the ravine makes more sense.

There are many prostrate pine and hemlocks and others that will grow down the embankment . I have a (Japanese Pine) Pinus Densaflora Prostrate coming down a small hill side, (Scots Pine) Pinus Sylvestris Albyns or Hillside Creeper would grow in a similar way. Also there are lots of Tsuga's (Hemlocks) Like Kelsy's Weeper or Coles.
I grow all these in my yard, like you zone 5 IL

Ravines are hard to maintain. That's going to be your main problem.
Both initially and on going for years. How stable are the banks? Water in the bottom increases the maintenance problem.
Building a structure to hold your tree is the next problem.
Are you sure you want to do this?
A picture of the site would help, even if it's full of brush. Try your best to get the best angles.
Mike

We've been keeping a close eye on the banks, Mike. There's been heavy rains this spring/summer with minimal, if any, erosion. A soil and conservation guy came over and pretty much told me to relax about it. We put a few ground cover junipers along the upper slope disturbing only the planting hole area and leaving everything else alone. We've cut around those plants once this summer to make sure they get adequate light. If we plant a few things each spring, we're hoping the previous year's plants along with the 'weeds' will be enough to maintain stability.

This summer we've been replacing the fence (223 posts and counting) and since we're currently heading into the ravine, I've been pondering ways to give it a little 'Wow' factor...lol. Boy, what I'd love to do with a crane and a lot of limestone slabs...double lol.

Thanks for the cautionary advice; I sometimes need it.