Shooting Outside, in the Sun

[keylight]

we've done that once before

Can you share a short clip showing the results? Thanks!

[DDirector]

Yes, but its not lighting the subject(s) that is the biggest concern. You can bounce light at them, or flag some light off or scrim it down.
Its the issue of having them in a setting where the BG has both sunny and shaded parts.
It feels as though the sunny parts are over and shaded are under. While character is well exposed

Its more or less exposing for the sunny side, but a tad under. The shadows will be slightly brighter then, and the actors (if under the shade) will not be too under exposed.
In respect to the IRE scale, if I recall correctly, skintone should be at 70IRE (I could be wrong) and if the subject is in the shade with sun behind them. They wont be at that 70IRE, but lower. If they were, the sun would be way over exposed then.

So, basically, what IRE is acceptable for skintones, outside in the shade?

Its a different situation if the subject is in the sun, and there is sun/shade behind them. The sun would also be well exposed, but then the shade would be well underexposed.
If subject is in the sun, this is where scrims or large diffusion comes in to reduce/soften light. Its more of the BG having too much over/underexposure - in this situation, it would be underexposure in the shadows

[RickyC]

Can you share a short clip showing the results? Thanks!

I just Grip buddy, last time I looked through a viewfinder was about a year ago. Don't have the clip, sorry :S

@DDirector-

Seems you've got one of those impossible shots, that you're either going to have to be exposed to the sunny side or the dark side. Have you considered shooting elsewhere? If you're stuck with that shot you may have to expose in between, and do some playing around in post. Hopefully what you're shooting with has good flexibility. Isnt there one camera out there that shoots HDR video?

[cpc]

A popular way to deal with bright exteriors with film (and high DR digital cameras) is to overexpose. Then printing down and underdeveloping overexposed emulsions leads to a low contrast look with washed (how washed depends on how much you overexposed) and not very dark shadows. Essentially, you are bringing shadow detail over the toe where there is full tonal resolution (linear density change over log exposure). You can do a similar trick with high DR digital cameras.

Unfortunately, DSLRs have very limited highlights range. (More on dynamic range here.) This means that overexposure won't work and highlights will clip easily.
You still have options though. For example, with Canon DSLR cameras, you can use ALO, Highlights tone priority or a flat transfer curve. ALO tweaks the transfer curve and opens up the shadows, HTP extends the highlights range a bit (it does a digital pull, trading off with increased noise in the blacks), and a flat transfer curve will allow more detail in the shadows (trading with mids detail), partly simulating the forementioned low contrast look.

Exposure-wise you can put skin 2 and even 3 stops over mid gray in bright sun (reflective readings). Except that your DSLR won't have that much latitude and will blow to white a little above 3 stops (around 3 1/3 for prev gen Canon cameras). Limited range aside, with incident readings, overexposing 1/2 to 3/4 stops is ok if you want to convey a hot feel.
With shadows, it is not unnatural to be 2 to 3 stops under in deep shade. You will have to do some tests and see what you like though, if you are set on a specific transfer curve just shoot a few headshots playing with exposure.

Also, avoiding midday may be a good idea. Shoot in the morning or late afternoon if possible. Lower sun will give more texture, better shadows and more manageable scene contrast range. Of course, this all depends on the location and what time is appropraite for your angles.