Not all skateboard tricks are created equal. Everyone has their own opinions on what looks good and what doesn't, but for many, the inward heelflip is a no go.
What is it about this trick that makes it so often look ghastly?
For starters, we need to point out our most agreed upon observation: this is a trick, that at it's peak often looks like a poorly timed snapshot of someone doing an Irish jig.
Then there’s the blurry line between inward heelflips and pressure flips. Often when someone busts one out in a game of SKATE, it's soon followed by a discussion of whether or not it was actually a pressure flip. If it's a trick that's often be confused for a pressure flip, you're going to have a problem.
This a trick that has a lot working against it.
First off, the inward heelflip is a varial trick, just like it's frequently dissed and similary hard to make look good sibling, the varial kickflip. For both, if they're too much in sync it looks like you’re hovering over a gyroscope, too out of sync and you’re working with a wonky pile of gross. Take a look back at how hard a stylish guy like Mike Carroll has to focus to get the board to flip properly. Your board simply does not like flipping and and doing a shove-it in the same direction, and it shows.
It also doesn’t help that the trick involves a heelflip. It would be hard to put a number to it, but the skate world is not full of what could be called natural heelflippers. Lots of people can pull them off, but it's a vast minority that can make them look as good (or better than) a kickflip. Not unlike a kickflip, a proper heelflip should be flicked and the people in possession of that proper heel flick are comprise a short list. C.J. Tamborino and Wieger van Wageningen come to mind (possibly something in the ginger DNA?) among the few.
There are in the world, however, other well executed examples. The most prominent of them come from people like Karl Watson and Antwaun Dixon, people who look relaxed on their skateboards. People who are no strangers to yoga or appearing partially asleep while skating. It’s hard to place too much weight on these guys in general, simply because they're the type that can't seem to make any trick look bad. Moral of the story: if you have the ability to look spastic on a skateboard, you are not in luck with this one.
And yet, the inward heel finds even more places to redeem itself. The more open road to an attractive inward heelflip is to do it nollie or switch. Those who can do them in these more challenging ways seem to be able to do them without succumbing to the fate of the standard variety of the trick. Is this because switch tricks rarely look as efforted as standard ones? Or is it simply because if you're good enough to land one of these switch, you're good enough to make it look proper?
All we know is that if someone busts out an inward heelflip in a game of SKATE, they're probably not your friend.