during the X Games on June 27, 1999, the eyes of hundreds in attendance fell on a frustrated and pained Tony Hawk.

The skateboarder was attempting a 900, at the time considered the sport’s Holy Grail, which would require him to speed up a halfpipe into the air, turn his massive 6-foot-3 frame two-and-a-half rotations (900 degrees), and land with his feet firmly on the board. It had never been done in competition before.

It was the one move that Hawk, then 31, desperately wanted to land, but one that had eluded him for nearly a decade. Though the legend was well established within the action sports community — Hawk turned professional at 14, had secured four gold medals, two silver medals and a bronze at the X Games and was referred to as the “Babe Ruth of Skateboarding” — the 900 remained at the top of his bucket list, even if the pursuit of it had already cost him a broken rib, lost teeth, back injuries and several concussions over the years.

“It’s something that I had been attempting on and off for almost 10 years prior to that event and had tried my hardest to make it,” Hawk, now 51, tells PEOPLE. “I had definitely put myself out there to try to make it over the years, and had a few injuries, and got really close a couple of times.”

Yet, heading into the Vert Best Trick Finals at the fifth X Games, the 900 wasn’t part of Hawk’s gameplan. He initially intended to perform one difficult trick he had landed before, but when he successfully pulled it off earlier than expected, he was left with time to improvise.

“How it played out was that I actually made that trick early on, and then I made another trick that I had in mind that was a little bit harder,” Hawk, from Carlsbad, California, recalls. “But once I did those — those were literally my best tricks — I still had time left in the event.”

“I don’t remember exactly how it played out,” he continued. “But someone told me that the announcer, Dave Duncan, was the one who suggested that I should try a 900, because he knew that was something that I had been trying over the years.”

With Duncan hyping up the crowd, Hawk hit the ramp with zero expectation that history would be made that night.

“There was no intention of making it on those first few attempts,” recalls Hawk, who was the first skater to land a 720 in 1985. “It was more like, okay, here’s the trick that I wish I could do, and this is what it looks like.”

The first few tries saw the board fly out from under his feet just as he came out of the final spin, which sent him sliding to his knees. Still, the crowd and his rival skaters cheered him on, and spin after spin, fall after fall, Hawk’s confidence grew.

“After the first four or so attempts, there was a certain consistency to my spinning and my speed that I had never had before, because the ramp was built so well. That really was what I attribute that to, that I was finally riding a ramp that was consistent and fast,” Hawk explains, adding that many ramps were “very rickety” in the 1990s.

“Every time I tried it, it felt the same,” he continued. “That had never happened for me before. So I started to realize that maybe I can actually start trying to land these, and then I started to try.”

During the next few runs down the halfpipe, Hawk made small adjustments, first by shifting his weight through the spin so he could lean further back and not fall forward. But this caused him to lean too far back on another try, so he decided to “split the difference” in how much he would shift his weight.

“That was the moment that I knew that it was possible,” he recalls.

Then, after 11 tries and a decade of anticipation, Hawk sailed up the pipe, spun two-and-half times and hit the landing, winning the gold medal and becoming the first person to complete a documented 900. The skaters there to compete against him quickly embraced Hawk, who lifted both arms triumphantly in the air. He defied gravity and surpassed limitations.

“It all seems very simple in hindsight, but that’s what it took, was having a ramp like that, and having the support of my peers and the crowd was hugely important,” Hawk recalls of the moment, one that would go on to not only become a defining moment for him, but one for the entire sport of skateboarding, even if he didn’t realize it at the time.

“What I felt was just a great relief. I didn’t feel like I had accomplished something monumental in terms of anything outside of skateboarding,” Hawk says. “It was just more of a personal goal, and it was just this great relief, like I had this weight off my shoulders. I didn’t have any idea how it would resonate or the ramifications or awareness that it would bring.“

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Shortly after landing the trick, Hawk officially retired from competition after winning more than 70 contests throughout his time as a professional. The X Games would later call the feat, “arguably the most famous moment in action sports history,” cementing a storybook ending to a 17-year career.

News coverage of the milestone quickly made Hawk a household name to many outside of the skateboarding community, and it was something that initially came as a surprise to him.

“People who had never set foot on a skateboard were complimenting me on doing a 900, and it just felt surreal,” he recalls. “It was definitely the highlight of my competitive career… definitely a turning point in my life.”

Two months later, Hawk’s video game, Tony Hawk’s Pro Skater, was released for the Sony PlayStation, and the popularity of the title and Hawk’s newfound fame propelled skateboarding’s influence in everything from clothing to music.

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In the years since, the skating legend has used his organization, the Tony Hawk Foundation, to give away over $5 million to 556 skatepark projects around the United States that will help cultivate the next generation of skateboarders.

“Skateboarding is the great equalizer. And when you go to a skate park, you see so much diversity, and you see people encouraging,” Hawk, a father of four, says. “And you see the camaraderie, because even though it is very much an individual pursuit, even though we do have competition, I feel like it’s much more an art form than a competitive sport.”

Next year, skateboarding will be making its debut at the 2020 Summer Olympics in Tokyo, Japan. Naturally, Hawk was outspoken in efforts to get the sport included in the games, not because skateboarding needed the Olympics, but because he believed the Olympics needed the “cool factor” of skateboarding.

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Only a handful people have landed the 900 since Hawk pulled it off in 1999, the youngest being 10-year-old Asher Bradshaw in 2014. Hawk, himself, would go on to hit the 900 a few more times, with the most recent two coming at the age of 43 in 2011, and another in 2016 at the age of 48. While he billed the latter as the last 900 he would ever attempt, when asked, he left open the possibility for another.

“I didn’t expect it to be such a struggle as it was, and so at that moment, I very much felt like that’s the last one I want to do,” Hawk says with a laugh. “But, you know, now that I’m a little bit further away from that moment, who knows?”