- First took to skateboarding at just 18 months old, when he found his father's old board in the family's garage.
- Wrote Tony Hawk a letter inviting the skateboarding legend to his 7th birthday party; Hawk actually came and showed Sheckler some moves.
- Won a number of California Amateur Skateboarding League state titles before turning pro.
- Broke through as skateboarding's then-youngest ever professional in 2003, winning top honors at the X Games, Gravity Games, Vans Triple Crown and Slam City Jam.
- Developed a signature move called the "Sheck-lair," which Sheckler describes as an "indy kickflip flyout."
- Landed his own MTV reality show, Life of Ryan, in 2007.