- “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]
Herbert Edwin "Herb" Powell is Homer Simpson's seldom-seen long-lost older parental half-brother. He was first mentioned by Abraham Simpson when Homer comes to his side after he suffers a heart attack. Herbert is also the half-uncle of Bart, Lisa, and Maggie.
Herb was overjoyed when he found out about his long lost half-brother. He made sure his family felt right at home and got along great with Marge and the kids. His relationship with Homer went bad after the car he designed ruined Herb's company. However, after his success again, he forgave him, and was happy to call Homer his brother, which was what both had wanted.
Herb is an intelligent, ambitious, charismatic, passionate, but also lonely person. Unlike his half-brother, he doesn't have a family to share his life with, but learns how to love a family from meeting the Simpsons. He doesn't have his employees total respect however as he's very assertive when it comes to business, but he is a good businessman and seems to be pretty optimistic that a man can make it big.
The product of a short-lived affair between Homer's father, Abraham Simpson, and Gaby, while Abraham was courting Homer's mother, Mona, 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 $2,000 (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", although much more hidden.
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 lost his wealth again, although the circumstances behind this misfortune were not explained.
Herbert Powell got his fame by making and designing cars at Powell Motors but lost his fame after he met his half brother Homer Simpson when he asked Homer to make a car of his choice. The car was called "blunder of the century," due to the car looking ridiculous and costing $82,000. This sent the company into bankruptcy, and Herb to the street.
Herb's biological parents are Abraham Simpson and Gaby. 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. If Abe's story about Virgil Simpson is true, then Herb is 1/32 Black.
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.
Herb is voiced by Danny DeVito (Oh Brother, Where Art Thou? and Brother, Can You Spare Two Dimes?). After Brother, Can You Spare Two Dimes? Herb does not appear again until The Heartbroke Kid where you can see a picture him, then again in Changing of the Guardian where he is voiced again by DeVito (single line, voice only).
- Herbert punched Homer in the 1991 episode.
- Herbert's car has been used in 'The Simpsons: Hit & Run' and 'The Simpsons Road Rage'. It also appears as a decoration in tapped out.
- Herb does not know about his half-sister Abbie, probably because Abe and Homer didn't know about her until they went to England.
- Herb does not make physical appearance in "Changing of the Guardian", but is heard over the phone when Marge and Homer turn to him as guardians for Bart, Lisa and Maggie. Also, it revealed that he went poor again.
- Herb was given an indirect reference in The Simpsons Road Rage with the selection screen for The Homer, where Homer says "And the sticker price... is $82,000?!" and accompanied by multiple shocked gasps from a crowd and La Cucaracha playing in the background, alluding to the events of Oh Brother, Where Art Thou? and more specifically the unveiling of The Homer and Herb's reaction to learning the sticker price.
- Episode – "Oh Brother, Where Art Thou?"
- Episode – "Brother, Can You Spare Two Dimes?"
- Episode – "Gump Roast" (clip in end song)
- Episode – "The Heartbroke Kid" (seen in picture)
- Episode – "Changing of the Guardian" (Voice only)
- Video game – The Simpsons: Tapped Out
- Comic book – Uncle Burn$ (seen in picture)
- Comic book – Formula for Disaster (mentioned)
- Comic book – Homer Fries! (mentioned)
- Comic book – Simpsons Comics: Get Some Fancy Book Learnin'
- Book – The Simpsons Uncensored Family Album
- Couch gag – "Sgt. Pepper's Lonely Hearts Club Band couch gag"[src]