Max Simkin (Adam Sandler) is a lonely cobbler with no social life, now running his father’s shoe repair business after his father walked out on the family years ago. One night, Max slips on a pair of customers’ shoes and discovers that any shoes that were stitched using his father’s old, manual sewing machine will transform you into that customer. Max gets a little out of control because while wearing his customers shoes he gets involved in a sinister plot involving the eviction of an old man from an apartment building by the local slumlord. Max’s mother also dies and Max’s neighbor Jimmy (Steve Buscemi) who runs the barber shop next door sees Max getting further into trouble. Jimmy tries to warn him of be careful but Max doesn’t listen.
After a violent exchange with Leon, one of the slumlords hitmen, Max accidentally kills him. He goes to the police to tell him about the accidental death but Leon’s body has disappeared and they cops don’t believe Max. Max finally realizes someone may be helping him but that he has to help himself to clean up the mess he made. He works with Carmen, the young lady who has been trying to save the residents from being kicked out of their homes by the slumlord, and through an elaborate plan and the use of many customer’s shoes, Max frames the slumlord and her violent and illegal activity are caught on camera. She is arrested.
Back at the shoe repair shop, Max agrees to a date with Carmen. Jimmy reveals that he is actually Max’s father, but has been in disguise for years by wearing the real Jimmy’s shoes to be close to his son. The real Jimmy is alive and well and retired in the Carribean. Jimmy is the one who had been helping Max all along clean up the mess he was making and tells him that they are the “keepers of soles (souls)” and to use that power carefully.