Chad, I've found that water resistant headphones sound a ton better than the H2O waterproof ones. You don't need waterproof headphones for wakeboarding since you're not listening to music under water. I've tried a few standard headphones that are rated as "water resistant" and these are my favorite in terms of sound quality and fit:
http://reviews.cnet.com/Sony_MDR_G57G/4505-6468_7-20604865.html?tag=pdtl-list Since everyone's head and ears are different, some of these other water resistant headphones might work better for you:
http://reviews.cnet.com/4566-6450_7-0.html?filter=500909_5007939_ Jamie, give em a try, I think you might be pleasantly surprised by the superiour sound quality. I was amazed!