Say what you will about the iPod Touch being the poor-man's iPhone, this covetable, do-everything gadget has set the bar incredibly high in the MP3 player space. The Touch doesn't come cheap, but it's an excellent value considering all its features and its endless extensibility with a la carte iTunes apps.
Next up, the Chumby, another highly adaptable touch-screen gadget which uses software widgets similar to the Touch. The Chumby has moved around my house several times over the past year, filling-in as an alarm clock, kitchen RSS reader, and currently working as a Pandora Internet radio receiver in my living room. Yes, it looks weird, but you'll eventually become a little obsessed.
The iPod Touch is great for taking in video podcasts on my train ride to work, but it's a bit too small for watching movies in bed, and my wife hates the noise and glare caused by watching movies on my laptop. The Cowon O2 is a perfect compromise. For less than $300, the O2 offers awesome battery life, a decent-size screen, and more file format support than you'll ever need.
If you're like me and you like making music as much as listening to it, it's nice to have a handy, high-quality stereo recorder around to capture those brief moments of inspiration. The Edirol R-09HR is easily the best handheld recorder I've reviewed all year, offering tons of recording options and great built-in microphones.
If you're really like me and you like making weird electronic music, then Yamaha's Tenori-On music sequencer is right up your alley. The Tenori-On feels like a drum machine from another dimension, yet its game-like quality offers instant appeal.
Every now and then you need a turntable to play an old sentimental record or impress your hipster girlfriend. The Ion iPTUSB is my current fave because it's cheap, small, and works over USB. The audio quality is surprisingly decent and you can run it from batteries or the included power adapter.
Whether your music tastes run tame or extraterrestrial, you can't go wrong with a high-end pair of headphones. I've gone through three generations of Ultrasone cans and I can't say enough good things about the brand. I'm currently rocking the HFI-2200s at home, and their brown '70s living room aesthetic only hints at the plush, full sound they dish out.