- Endured two major surgeries before his first birthday, both to correct a heart defect.
- Mentored at the age of nine by skateboarding legend Tony Hawk, a neighbor at the time, at the Encinitas YMCA Skate Park.
- Nicknamed the "Flying Tomato" for his flowing, curly red hair.
- In 2000, debuted at the X Games at the age of 13.
- Missed out on qualifying for the 2002 Olympic team by only three-tenths of a point.
- Strung together four consecutive X Games gold medals in one discipline (snowboard slopestyle, 2003-06), the first athlete to do so in either summer or winter competition.
- Won his first U.S. Open at the age of 16.
- Won a gold medal on the Halfpipe at the 2006 Winter Olympics in Turin, Italy.
- The first athlete to qualify for both the Winter and Summer X Games in unique events.
- The first athlete to win both a Summer and Winter Dew Cup.
- Repeated his Olympic success and won gold again on the Halfpipe at the 2010 Winter Olympics in Vancouver.
- Cut off his signature hair in 2012 to donate it to Locks of Love, which makes hairpieces for children suffering from cancer.
- Has made cameo appearances as himself in films and TV shows, including Friends with Benefits (2011), Da Flippity Flop, American Dad! and Cloud 9.
- Has also performed in an electronic rock band called Bad Things, playing the guitar.