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I average about 100 flights per year.
I use a 80gb ipod (music only) with Shure E4 in-ear isolating headphones (about $300 – but worth it!). I love the size and sound quality of the E4’s.
For short flights I just try to sleep (and try to plan the flights to fall within good sleeping times) as I find it too much hassle to perform big “setups” of technology. You have to keep the cramped space in mind when deciding how to occupy yourself. So my routine for a <3hour flight is to (1) get a window seat (to avoid getting your elbow or other body part crippled by the drinks cart or other passengers), (2) put on my E4's (with or without music) as soon as I'm seated, and (3) sleep. One of the best things about noise isolation headphones is to eliminate the pre-flight safety drill!
For longer flights I take my Sony PSP. The quality and the number of games available for the PSP is disappointing. But I rip a bunch of movies to the PSP and unlike a laptop, the battery lasts for more that one movie. You can also use additional memory sticks and batteries (some of my flights are over 20hrs!). I also carry an audio splitter cable so the wife can watch with me.
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