| Herbert "Herb" Powell|
|Occupation|| CEO of Powell Motors (formerly)|
|Relatives|| Parents: Abraham Simpson and an unnamed carnival woman|
Adoptive parents: Edward Powell and Mililani Osler
|First Appearance||"Oh Brother, Where Art Thou?"|
|Voiced By||Danny DeVito|
- “This is America, and in America, you're never finished as long as you have a brain in your head, because all a man really needs is an idea.”
- ―Herbert Powell[src]
- “Hi, you've reached Herb Powell. I'm poor again.”
- ―Herb's answering machine.[src]
- “Bart, Uncle Herb sounds too formal. Do you think you can call me "Unky Herb"?”
- ―Herb telling Bart to call him "Unky Herb".[src]
The product of a short-lived affair between Homer's father, Abraham Simpson, and an unnamed female carnival worker, Herb was adopted by Edward Powell and Mililani Osler. He put himself through Harvard by working odd jobs because his adoptive parents refused to pay for his admission (or may not have been able to afford his college tuition). He then founded Powell Motors, a car company based in Detroit. Herb was overjoyed to learn that he had a birth family and bonded with his nieces and nephew, and - in his role as CEO - allowed Homer to design a car. However, Homer's car was a failure and it bankrupted the company. Herb ended up becoming a street vagrant. He prefers to be called "Unky Herb" by his nieces and nephew, because he thinks the term "uncle" is too formal.
He briefly settled in the Simpson household, despite his intense continuing antipathy toward Homer. Homer loaned Herb $2000 (from the power plant, as compensation for making him sterile from radiation), which Herb used to build an invention that translated infantile speech into comprehensible English, based on observations he made of Maggie Simpson. He proceeded to mass-produce his new product and regained his fortune. He then proceeded to pay back the Simpson family the $2,000, but also bought Homer a vibrating chair, Marge a new washer and dryer set, Bart a life membership in the National Rifle Association, Lisa a monthly set of classic novels, and a promise that he will buy something nice for Maggie. Most of all, Herb ends his antipathy towards Homer and is happy to call him his brother once again.
While far smarter and more successful than most other male Simpsons as well as having a trim figure and full head of hair he still does exhibit signs of the "Simpson Gene" which manifests more as lapses in judgement than outright stupidity such as allowing his brother to design a car and holding Maggie above his head while she was clearly about to spit up.
Herb does have cameo appearances such as when he appeared in a picture as Homer was listing off family members who needed to lose weight. Homer referred to him as "my seldom seen half-brother Herb". He considers wealth in terms of love and family, not money. According to Danny DeVito, he will be voicing Herb again in a reappearance that is set to occur sometime in season 24. Though he did not make a physical appearance in Changing of the Guardian, his voice was indeed heard for a brief second in the episode. It is revealed that he has gone poor again.
Herb's biological parents are Abraham Simpson and an unnamed woman. Abe first met the attractive female prostitute at a traveling carnival, where they were taken with each other. One year later, Abe saw the same woman again at the carnival to find out he had fathered an illegitimate son (Herb) with her. Unmarried and ashamed, Abe and the woman took their infant son to the Shelbyville Orphanage, where he was later adopted by the Powell family. A year later, Abe married Mona and Abe told Mona about what happened at the carnival. When Homer was born, Mona told Abe to never tell Homer about the out-of-wedlock birth. However, Abe had a mild heart attack in his senior years and decided to tell Homer about Herb.
Herb has a younger half-brother, Homer, and possibly an older half-sister, Abbie. Abbie could be the product of an affair Abe had during World War II. While Abbie is never explicitly called a Simpson, she looks and acts just like a female version of Homer.
Herb lived at Shelbyville Orphanage. Herb was adopted by Mr. Edward Powell and Mrs. Mililani Osler . Mililani also gave birth to Coco Powell, Wanda Powell, Carla Powell. Sometime before Herb met Homer, Edward and Mililani told Herb he was adopted, which upset Herb as it left him with no feeling of having a family.
- Episode – "Oh Brother, Where Art Thou?"
- Episode – "Brother, Can You Spare Two Dimes?"
- Episode – "The Trouble with Trillions" (mentioned, but not named)
- Episode – "The Heartbroke Kid" (mentioned)
- Episode – "Changing of the Guardian" (voice only)
- Comic book – Battle For The Barks Billions (seen in picture)
- Comic book – Bart Simpson 71 (mentioned)
- Couch gag – "4F06"[[|[src]]]