For the sake of this long awaited Zaturdays, it’s probably not worth the trouble to get caught up in the debate about what it means to be the “best” in skateboarding. I know, there’s no such thing because skateboarding is an art not a sport, style is subjective (but still matters more than anything), different tricks are hard for different people for different reasons, etc. So the “best” is a term that can only be used loosely and should be used for entertainment purposes only.
BUT…

if we’re going to be real, we have to agree that some people are better than other people at skateboarding. Tricks, style, attitude, longevity, weigh of one’s contributions, etc. all contribute. That said, I don’t think there can be much argument or debate that there are two people that have been better at skateboarding than all the other people that have ever given it a go, and they are Tony Hawk and Mark Gonzales, in no particular order.
I could write a book about why Hawk is the best, but in his case that book has already been written and it’s called Hawk, Occupation Skateboarder. You should read it. Hawk won almost every contest he entered for about 20 years straight, including the first Xgames in 1995. He invented something like a million tricks, including the stalefish, the Madonna, the 720 and the 900. He’s filmed cutting edge video parts since 1984 and still cranks them out. He did a 900 at 48. Oh, and he’s willing to slam his brains out still, like when he did the 900 at 48. He can grind handrails, launch boxes, and star in commercials. He started Birdhouse skateboards, supports a ripping team, and has a kid that’s a pro skateboarder. There’s also his role as spokesperson and advocate for all things skate, and his Tony Hawk Foundation has built parks all over the entire world. Tony Hawk is the best.
When TWS put out their 30 Most Influential Skaters list a few years back, Mark Gonzales topped the list, even ahead of the Birdman, and I didn’t hear even one of us opinionated skaters take issue with it. That pretty much says it all. In this case, influential is synonymous with best. Gonz has been on the scene nearly as long as Hawk and filmed some of the first and most innovative street parts ever. He pioneered almost every trick he was doing (for an idea you can peep Video Days where virtually everything he did was NBD). He abused the transitions as much as he did street and to this day his personality embodies what it means to be a skateboarder. Gonz also just recently jump slid a handrail on a briefcase. Mark Gonzales is the best.
So you get the idea. But since we all love to round out the podium with a top three, the question becomes, who’s third best? That’s where it all breaks down. TWS had Rodney Mullen as the third most influential, and I can’t argue with it, but does that mean third best? Is it possible that the three best in the history of the world were all born within like one year of each other and came up in the exact same era? While it’s true that Mullen invented a zillion of the tricks we still do (or at least try to do) today, he never skated handrails, never ripped transition, never topped the style charts. What about Tom Penny? He pioneered the act of going huge while keeping it casual. Pat Duffy was the first to grind the monster rails that are commonplace today. Gino Iannucci was every pro’s favorite and had one of the most aped styles of the 90s. Shane O’Neill can get his skateboard to do anything he wants it to, like nothing. Koston was Shane O’Neill before Shane O’Neill was. Nyjah Huston wins everything and can do all of his tricks every try. Chris Cole won SOTY twice. Salman Agah pretty much invented switch stance. Ishod can skate for 10 hours straight and do impossible tricks the whole time and never fall. Have you seen Grant Taylor roll around in a bowl? Jaws ollied 25. Then there’s Cardiel, Danny Way, Bob Burnquist, Matt Hensley, Reynolds, Guy, and Daewon. Oh! What about Suciu?

Long story short, the third best skater might include a list of 100s. Who’s your pick, and the better question might be HOW COME?