Quote:
Backgrounds, although a necessary evil, can be awfully frustrating for me.
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A necessary evil? OUCH! Methinks I've found your problem! You need to reorient your thinking. Think of the background as that which supports your main focus. You need air around you to breath, don't you? So do the heads you paint. Every yin needs its yang. Think in complementary terms. What colors, shapes and values will make the key foreground elements come to the fore while harmonizing with it.
In the most simple terms, the background is a part of the shadow realm; it balances the light. This is regardless of whether the background is in shadow or in light. The reasoning behind this is that the atmosphere inhabits both the background space as well as the shadow realm.
If all else fails you could just do vignetted paintings on tonal backgrounds. This is a technique that some of todays most renowned and successful Alla Prima portraitists regularly employ.