I had a similar experience to Evan's on my Tokyo-Chicago flight. The flight was about half full so we could stretch out and I had three Tylenol PMs and 3 bloody mary's in my system, I was comatose for 2/3rds of the flight. Same thing on my last Hawaii to US flight. Three tylenol Pm's and I do not remember a thing about the flight.
Mixing alcohol with sleeping pills (or something roughly equivalent) probably isn't the best of ideas. The few times I've braved long Greyhound/Train rides I've found staying up all night beforehand works pretty well. I would also try to bring a pillow, earplugs (or better yet noise cancelling headphones pumping quite Sigur Ros tones), and a hat with which to block to sun. That pretty much amounts to sleep for me, though as Evan can attest I can sleep in pretty rough conditions.
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