The heelflip, is an aerial skateboarding trick where the skateboarder kicks out in front of him/her flipping board360 degrees along the board's long axis. A heelflip is executed similarly to the ollie, and like the ollie has become a defining trick of "New School" skateboarding.
Execution
A heelflip is the opposite of a kickflip, as the board spins towards the toes. For a regular skater the board spins clockwise from the perspective of one behind the skater. Again, there is a kick as part of the ollie but unlike the kickflip it is directed forward and outwards away from the rider's toe side, so that the last part of the foot to leave the board is the heel, hence the name.
Variations
Variations and extensions of the standard heelflip are very common - some of these are:
Double Heelflip, where the board flips twice before being caught.
Triple Heelflip, where the board flips three times before being caught.
Heelflip Body Varial,, where the skater does a backside 180 turn, while the board does not spin, but still flips.
Varial Heelflip, where the board does one heel flip, and spins 180 degrees frontside at the same time.
Late Front-Foot Heelflip, in which the tail is snapped and the ollie is pursued but, at the peak of the ollie the heel of the front foot pushes downward on the toe-side edge of the board causing it to rotate once.
Late Heelflip, in which the rider does an Ollie, and at the peak of their air they flick their back foot resulting in a Heelflip.
The Heelflip Grab, a variation on grabs where the rider flips the board and catches it with his hand rather than the feet. It was first done on a vertical ramp but now is very commonly seen done on launch ramps or other surfaces which can generate sufficientair time.
Inward Heelflip, a combination of the backside pop shove-it and the Heelflip, this trick is usually executed with the crossing of the skater's legs. The opposite of a Hardflip.
Bigspin Heel, the skaters body does a frontside 180 while their board does a laser flip.