I first experienced significant ear pain when flying when I was in college in 1985. The pain usually occurred on takeoffs and landings. However, around 1998 I discovered these little ear plugs that prevent rapid pressure changes within my ears. Since using them I have never again experienced the extreme pain from depressurization, and I can fly free from pain.
Earplanes are slightly different than normal earplugs, and include a ceramic pressure regulator that slows the pressure changes between the inner ear cavity and the airplane cabin. They are a little more expensive than normal ear plugs, but they have made flying tolerable.