Hiring a Top Dollar Pro SkateboarderBig names like Tony Hawk and Rob Dyrdek can be hired for your events! Of course, these guys don't come cheap - at the time I'm writing this, Tony Hawk is listed at $60 to $80 thousand dollars! BUT, having Tony Hawk show up at your company's event or holding your brand of toothpaste might make you a huge pile of cash!
Rob Dyrdek goes for a little less, and a pro skater like Bam Margera goes for as little as $10 to $20 thousand dollars. So, it depends on what sort of quality you want! But, if you are looking for a well known pro skater, plan on spending some real money.
Here are some websites to check out for booking and hiring pro skaters:Pro Skateboarding tap, you can see interviews with several pro skaters. These might give you an idea of who more closely matches what you are looking for.
These same companies above can also be used to find cheaper pro skaters - pro skaters who might be less known, but who are still excellent, and who could be used for parties, films, and that level of entertainment. Groups like SSA Freestylers in the UK, and the groups above, can all be used to find moderate pro skaters as well.
(if you're confused about the term "pro skater", and what defines it, don't feel out of the loop - read What Makes a Pro Skater Pro?)
Hiring a Skateboarder Demo TeamThere are several companies and skateboarding teams out there who rent themselves out to do demos, and they can be a great choice for smaller events ("smaller" is a pretty loose term here! Anything from a festival to a party to a fun school function might work!).
These demonstration teams, or "demo teams", can be hired from all over the place. For example, the 3rd Lair skateboard team travels all over the upper Midwest to do demos, clinics, and anything else that you might want them for. And their prices are very reasonable.
If you're looking for a team like this in your area, the best place to start is by calling up your local skateboard shops and private skate parks and asking if they know of any. Private skate parks and local shops often have teams just like this 3rd Lair team, and you might end up with a good team for a great price (or even free, if you let them promote their business!).
A word of warning here, though! Ask for some kind of reference. This might be someone who hosted their team previously, or anything, really. It's just good to make sure that the group will actually be entertaining, and won't turn out to be a waste of money.
And, there are a LOT of them out there. Check out my Christian Pro Skaters Demo Teams list to see for yourself. Chances are, there's something in your area and price range. And if you really don't want them to bring in their beliefs, you can always ask them not to. The worst that can happen is that they'll say no. Or, that they'd just do it anyway, but these groups have reputations.
Hiring a Kid with a SkateboardAnd last, just in case you haven't thought of it, you could simply hire any old skater. Most towns have a lot of VERY talented skaters who are underground and unknown to the general public. If you hang out at your local skateparks, you can sometimes see skaters who will blow your mind! You wonder why they aren't pro, and the answer is usually complicated.
So, to hire one of these type of skaters, or a group of them, you can post an add at your local skateparks, at your local skateboard shops, or on Craiglist. If you go through your local skate shop, then the owner of the shop could likely suggest some skaters who would be interested, and who would match what you are looking for. You might even be able to get the shop to give away a few T-Shirt of stickers, to help promote their shop!