Mail? It ends up being ~alive~. The skateboard sounds like a computerized Microsoft Sam style voice. At the end he impresses a bunch o bullies by doing something impressive on the skateboard? Something like that... Anyway, what was this movie! I remember it fondly haha.

Try The Skateboard Kid

The Skateboard Kid (1993)

http://www.imdb.com/title/tt0108153/

The skateboard kid is not the right movie, but I know what the asker is talking about. I too can't remember the name of that movie but am trying desperately to remember

Yes,this is the movie you are looking for.
Plot Summary for
The Skateboard Kid (1993) More at IMDbPro »
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No one could be more bored than Zack, the new kid in town with no friends in sight. When a gang of hip, skateboarding thrashers start cruising his neighborhood, Zack hopes his luck will change. But they want nothing to do with him. Then Zack makes the discovery of his life: a talking wisecracking, magical skateboard. And suddenly, skateboarding rises to entirely new heights.

The movie I remember had a kid that ordered a skateboard in the mail that was computerized and talked. The kid in the skateboard kid did not order it, he created it.

Furthermore, in the movie I'm looking for the skateboard went out on the kid right before a competition and he had to do the runs on his own without the power of the skateboard during the competition.