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The ollie is the base for nearly every modern skateboarding trick out there today. Not mastering the ollie means cutting yourself off from a whole cornucopia of stunts and gimmicks, not to mention that it makes navigating street terrain much more easier. For most skateboarders the ollie was the first trick they set out to learn and can recall countless hours spent in their driveway hopelessly flopping around. You can get an edge on the ollie and read this article!
Naturally before starting to attempt this you must first have a skateboard and a pair of shoes. All other clothing is optional but may come in handy for when you take your first bails.
Start by rolling at a comfortable speed. You could try this trick standing still but your not going to encounter many situations where you have to ollie in place, and by the time you do encounter that situation it will be no problem at all so just suck it up and start rolling.
The ball of your back foot should be positioned close to the edge of the tail, while still being comfortable enough to maintain balance. Some people even position it at an angle but that's all a matter of style. Your front foot will best be suited around the middle of your board, with a little bit of heel hanging off one side.
Jump off of your back foot, giving your board a nice solid "pop", and start sucking up your knees. The front end will rise up and your going to want to "roll" your front foot up to meet it to level your board out and send you air borne.
This "roll" is achieved by dragging the side of your shoe up against the grip tape. (This is how skate shoes get tore up so easily) Your foot will be angled at about the same degree the front of the board is rising. If this still doesn't make sense, (I don't blame you) then watch closely at a friend doing an ollie next time you go out and skate and you will see exactly what I mean. (Skate videos work fine as well)
What makes learning the ollie hard is that the roll has to occur almost instantly after the pop, which is hard for new-comers to the sport, but rest assured you will gain the muscle memory for it soon enough.
Suck up your knees a bit, this will make your ollie higher and make you look cooler and the tail end of your board will meet your back foot hopefully right over the bolts. With practice you won't even notice the back end of the board and the whole ollie will be one solid movement.
Prepare for landing. Unless your one of the brave few who wants to learn how to ollie off of a ledge then this should only be a matter of keeping centered above the board. Don't lean back, and don't lean forward. Just ignore the fact that your moving and make the skateboard your center of reference.
When your wheels touch the ground roll away with the satisfaction that you are well on your way into the wonderful of skateboarding, and if you didn't get it this time then keep practicing, nobody is perfect. Even people like Eric Koston had to go through the same rights of passage at one point, and never let any one trick get you down.
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