But that was still early days for Hawkcorp. Why he remains such a high-earner a decade-plus later isn't just about his physical abilities but, it seems, a combination of entrepreneurial drive, image control and branding savvy.
What's possibly ironic is that Hawk became head of his own empire - the building of which is described in his 2010 book How Did I Get Here? The Ascent of an Unlikely CEO - after skateboarding fell from favour in the early 90s.
Hawk, a professional on a skate team from his mid-teens, found his paydays further apart, especially with vertical skating out of fashion. He formed his own company and struggled until the advent of sport network ESPN's X Games which gave skateboarding a mainstream spotlight.
The coverage took Hawk from cult hero to action sports star, especially when cameras caught Hawk finally landing that 900 at an X Games on his 11th attempt.
As well as selling his own line in boards and clothing, Hawk built his own extreme sports touring show, the Huckjam series and produced his own skate videos - one of the Unlikely CEO chapters is entitled "Final Cut: The Key to Image Control is getting your own Editing Bay".
When makers of games for the PlayStation generation needed a name to put on their skateboarding titles, Hawk was the obvious choice.
Since the release of first title Tony Hawk's Pro Skater in 1999, there have been more than a dozen Hawk-endorsed console and handheld game titles, which have earned Hawk millions in royalties - though more recent incarnations have fallen from favour among gamers.
Still, if his later games haven't stayed on the cutting edge, the real Hawk is still flying. He's still landing 900s, among his many other freakish fearless moves of split-second timing and aerial grace.
And tomorrow, as he climbs the ramp ladder and drops in, Hawk will probably get more rock star adulation than the day's actual rockstars.
-TimeOut