On June 27, 1999, Hawk became the first skateboarder to land a "900", a trick involving the completion of two-and-a-half mid-air revolutions on a skateboard, in which he was successful on his twelfth attempt. After completing the trick, Hawk said "This is the best day of my life." Following this feat, Hawk decided to retire from professional competition that same year, but he continued to perform at the annual X Games until 2003, when he retired from professional competition for good. In 2011, Hawk was still able to land the trick and posted a video on his Twitter account stating, "I'm 43 and I did a 900 today." On June 27, 2016, at age 48, Hawk performed what he claimed would be his final 900. In a video posted on the YouTube channel RIDE Channel, Hawk said, "Spencer was there on my first one, and now he was there on my last. Bye." after successfully landing a 900.
A video game series based on Hawk's skateboarding, titled Tony Hawk's Pro Skater, debuted in 1999. Since then, the series has spawned 18 titles so far, including ten main-series titles, four spin-offs, and four repackages.