Headphones that sound smooth and comfortable on a pillow?

If you lay on your side all headphones will clash with the pillow.

Lay on your back and you can use any headphone.

There are speakers that fit under the pillow. They provide poor mono.

Why not a bedside audio player?

http://www.head-fi.org/newsearch?search=Yuin+PK-2

Erik - See link above to HeadFi.org and info on the Yuin PK earbuds.  They are not IEMs nor ar they conventional headphones.  The Yuins have very good sound and reasonable bass for their size.  They do require lengthy break in for what bass they produce to be realized.  I own the PK2s and listen to Pandora while falling asleep.  They are extremely comfortable.  I have woken up, forgotten I had them on and was startled to hear music playing in the room.  They "do" a big soundstage.  Worth consideration, I think.  Good luck with what sounds like a procedure you'd probably rather avoid.    

Thanks everyone!

Try in-ear headphones.

I know you said no IEMs, but the Weston W60s are perfect for your request.  They are smooth, they sound freakin awesome IMO.  And there is not issue with laying on the side of your head with them in.  

Guys, Many folks neither want an IEM/bud, or they don't fit their ears.  I have CIEM"s (Empire Ear Phantom's). I also own and will be selling (don't use can's anymore) my ZMF Ori's.  I love the CIEM's and dont' need more.  Some just want a can to listen while in bed.  The biggest question that folks should be asking is what is your source/amp.  Can't figure out the rest without knowing that part. 

I would think you'd want over the ear headphones so they're not applying pressure directly onto your ear, You would want something with a good thick pad but a flatter headband. I've seen some Sennheiser's that might work well. Also, Grado makes an over (or on) the ear headphone called the eGrado that's an around the back of the neck style. You could probably order a pillow that's softer or allows you to control the fill to adjust for your headphones. My wife and I bought pillows from a company called Nest Bedding Easy Breather Pillows. The concept behind these pillows is that you can unzip them and remove fill (put the extra fill in a ziplock bag and store away in your closet) to adjust them to your liking. You can find these pillows at buy one, get one half price. I would suggest you consider one of these pillows in combination with a over the ear headphone with a good quality cusion surround and flat headband. I've read your posts for years and know you like your music. If you need a headphone amp, I have a Schiit Lyr that I never use and would love for you to use it as long as you need it. I just don't use it (you can borrow my AKG K702's as well. I'm serious.) You just pay shipping, I live in Rochester NY. Let me know.