Weston Anderson is the youngest son of Dennis Anderson, and younger brother of Adam, Ryan, and Krysten Anderson. He started out driving the Bog Hog mud and mega truck before also driving King Sling. In 2022, he joined Monster Jam and Team Grave Digger, competing in Monster Jam Arena Championship Series East, using Morgan Kane's former Grave Digger 33. However, later during the season, he would receive Grave Digger 37, due to Grave Digger 33 receiving major chassis damage during the Hampton events.

Weston would ultimately win the tour in April at Southaven, MS, earning the first invite to World Finals 21. During the series, Weston also had a notable rivalry with former Monster Energy driver and current of Dragon, Coty Saucier. His run in the series for his rookie season would be considered to be the greatest rookie season for a driver in Monster Jam history by many, including Scott Douglass. Besides the World Finals, his first stadium show will be Edmonton Alberta on July 30.