Herb is the illegitmate child of Abraham Simpson and a carnival worker. A year after he was born, he was put into the Shelbyville Orphanage for adoption and was adopted by Mr. and Mrs. Powell, and was taken away to Detroit.

During his working years, he worked his way up from scrubbing toilets and cleaning dishes to owning a very successful car company, but he was tired of the boring meetings with the Board of Directors, concluding himself to be just a lonley guy as he has no real family.

While watching a McBain movie and having a heart attack, Grampa disclosed information about Herb to Homer. Homer sought to find him and did. Herb invited his half-brother to his mansion in Detroit.

Herb enjoyed spending time with the Simpsons, Bart in particular. And on trying to give Homer a car, he concludes that Homer would be able to help bring back profits to the company, by having Homer design a car, he has confidence in Homer that he does not wish to see the designs until it's finished. On completion he discovers that it costs $82,000 and it ruins the company, sending Herb into the gutter.

A year later, Herb discovers that Homer has won an "award" and a check for $2,000. Herb goes to Springfield, to ask Homer for his help in regaining his fortune. Herb comes up with the idea that will help babies communicate with a Baby Translator using Maggie as his source to gain translations. Homer reluctantly agrees.

Herb manages to regain his fortune and gives a gift to each member of the family. He finally forgives Homer for crippling him in the first place, and buys him a vibrating chair.