No one in full control of his or her senses enjoys going to the dentist. Those of us who are into high-performance portable audio do have an advantage over most folks - we can bring along our own portable pain reducers.
And, no, just because I do live in Colorado, I'm not referring to herbal remedies.
My pain-reducer is my iPod Classic 160 connected to a pair of Etymotic ER 4-P in-ear monitors. I've tried other combinations, such as using my Astell & Kern AK100 connected to Westone ES-5 custom in-ears. The Westone/Astell& Kern combo sounds better, but it's harder to get the ES-5 custom in-ear in and out of one ear so I can hear the dentist. Using the Etymotic ER-4P with a double-flange tip makes communication much easier since it pops in and out with less effort. And using the Astell & Kern AK100 when you can't look at its screen was tough - I kept touching things on the A&K's touch screen that I didn't want to touch.
Ergonomically, the iPod Classic 160 is perfect for no-look operation with its control wheel and centrally located enter button. As the sound of the drill gets louder I can increase the music's volume level by merely moving my finger along the circular control wheel in a clockwise direction. I love that.
As for music to get drilled by, I tend to lean more toward The Clash, The Who, and other music that beings with The. But most times, unless it's a scheduled root canal, let the iPod's shuffle choose the music. I figure I'd rather not begin to associate particular tracks with dental visits. That would be almost as joy killing for that music as if it were chosen for inclusion in my audio show evaluation collection.
So all you anti-portable audio audiophiles who write, "I never listen to headphones." Think about how soothing it could be to have "Live At Leeds" drowning out the hideous whine of a high-speed dental drill. Actually, in terms of value per minutes used, I can't think of any audio gear that's better than my "dental rig."
No it still doesn't make trips to that lean-back dental chair pleasant, but at least I have somewhere to go while I'm getting the treatment.