This is the gift they will love and despise, each and every morning. Clocky is a little alarm bot clock that runs away from you when you try to hit the snooze button. I know a few people who qualify for this gift, don't you? $45-$50 at Amazon.
How does it work? It is a wall-mounted lamp that is a replica of the moon. You can program it to mimic the real moon's cycle. It comes with a remote control for easy control. 
Does this hit you at the heart or what? One of my all-time favorite childhood memories - watching A Charlie Brown Christmas. You, too, can have your own pathetic tree, with one single red ornament included, for $24 at Urban Outfitters. (I highly recommend buying early. Last year they sold out by the end of November.)
Other notable Charlie Brown gifts...
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There are so many great uses for these antique typewriter alphabet stamps, like creating personalized greeting cards, labeling storage boxes, or decorating your wall with poetic words. For $5.99 this makes an exceptional stocking stuffer.
More collectible than toy, really, these wind-up tin toys continue to grow in popularity. With the overwhelming style options available, I recommend buying the ones that tell a personal story shared by you and your gift recipient.
I bought this Wind-Up Tin Ping Pong Toy ($24.99) for my Dad last holiday, because he was the one who taught me how to play when I was young. I was also privately reminding him about the awesome little fact that he was once a national champion player. Available at Mudan Boutique.