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$400 max eh? Okay, well whenever I've had to buy for one of those people who seems to have everything, sometimes one big expensive gift isn't really the ticket. Sometimes a lot of smaller gifts of varying sizes is the better way to go.
CDs
DVDs
Gift card (sports equipment store, etc)
Does he have the Fight channel? Is he into NHL hockey but doesn't have the NHL channel? Is there some pay channel he would like that he doesn't yet have??
Take him skydiving. Trust me, he'll love it. Tandem naked skydiving for the two of you -- even better.
Think of a few things he likes and buy him something to do with them.
Likes porn? Buy him a membership
Likes steak? Order him some Omaha steaks
Likes cheesecake? Order him a cheesecake of the month for a year.
You get the idea.
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