Born in Caringbah, Maddison grew up in Kiama Downs, and developed his passion for riding by competing in national motocross and supercross events.

Maddison continued learning freestyle motocross (FMX) tricks and after becoming proficient in the skills he entered his first amateur event,[which?]

On 1 January 2009, live on ESPN, Maddison and his Yamaha YZ 250 motorbike successfully jumped 96 feet (29 m) up onto the Arc de Triomphe in front of Paris Las Vegas and then descended an 80-foot (24 m) drop off the monument safely to ground level.

On 30 May 2009, Maddison indicated he was more than just a stuntman by defeating the world's best freestyle riders at the Calgary, AB, Canada stop of the Red Bull X-Fighters competition.

His victory in the Head-to-Head competition meant he had to progress through three rounds, defeating multiple X Games medallist Nate Adams (USA) in the first, defending series champion Mat Rebeaud (SUI) in the semi-final round and then 30-year-old series veteran Eigo Sato (JPN) in the final.

In April 2015 Maddison successfully rode a modified dirt motorbike on a wave near Teahupoo in Tahiti, after two years of preparation for the event.

[7] In 2017, Maddison appeared in the movie XXX: Return of Xander Cage, performing as a stunt double for actor Vin Diesel as he rode a motorbike on the ocean.

[11] Maddison's sponsors include Red Bull, Skullcandy, Swatch, Dunlop Sport, DC Shoe Company, Arnette, KMC, KTM, mophie, Parts Unlimited, Crusty.com, Stompgrip, Cernics, FMF Racing, VP racing fuels, Amerigas, Acerbis, Works Connection, Hammerhead, Pro Taper and Sony Action Cam.