Groundskeeper needs surgery

I'm searching for a movie, or possibly an episode of a TV show. A man promises to give his gardener insurance but can't afford it. When the gardener loses his fingers in a work accident, the man has to find a way to come up with the money for the surgery. I'm picturing Jason Lee as the employer, but that might be because the plot is similar to Stealing Harvard, or it might be an episode of My Name is Earl. I looked through Jason Lee's filmography but none of the titles stuck out to me. A little help?? Thanks!