I remember something about him stealing money from these two old ladies who sort of become his coach. It’s a comedy. One particular scene includes them making him a mouth guard out of hard candy (boiled sweets)

In the end he sort of become un-lazy and puts up a fight, its a feel good comedy movie.

Made in the 90s-2000s. I thought the main guy was played by seann william scott but apparently not. Any ideas?