He shares the same surname as Hubert H. Smithers, a character from Archie Comics who is the butler of Archie's girlfriend, Veronica Lodge.

It was implied once that something laid eggs in Smithers' brain and was considered serious enough of a medical issue that Mr. Burns, who had himself been discharged from the Mayo Clinic with a clean bill of health (relatively speaking) apologized to Smithers about his news, with Smithers himself stating that, since he considered the mere fact that even one egg was laid in his brain was "too many," he would "prefer not knowing" how many eggs were in his brain. [21] Smithers' official job at the power plant appears to be that of executive assistant, which he says is "actually about 2,800 smaller jobs", [16] responsible for monitoring employee attendance, is often a disciplinarian and has won dozens of "Employee of the Month" awards. [17] He has often hinted at wanting to be promoted to the position of executive vice president, but Burns has repeatedly squashed this dream, while whimsically bestowing the vice presidency on Homer [18] and a dog. [19] Although not a true hint, the end credits for " Dial "N" for Nerder" had among the "cast" Smithers dressed up in drag as the "wife" of Mr. Burns. (However, these may simply be because drag is relatively common in the gay community.) This version was published in The Utterly, Utterly Amusing And Pretty Damn Definitive Comic Relief Revue Book in 1989, and the topical references were getting a bit old even then. Smithers has the largest collection of Malibu Stacy dolls in the World and is the president of the Malibu Stacy fan club. As such, he also implies that he is a regular attendee at the annual StacyCon at San Diego in Airport Hilton with his statement of "Hello, Malibu Stacy Fans. I'll be seeing you at StacyCon '94 at San Diego Airport Hilton." [13]

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Smithers was originally brown with blue hair, as seen in " Homer's Odyssey". This was changed to his usual yellow skin with gray hair later in the series. Charles Montgomery Burns ● Waylon Smithers, Jr. ● Canary M. Burns ● Al Simmons ● Executive 1 ● Executive 2 ● Executive 3 ● Burns' Dog Vitti, Jon. (2002). The Simpsons season 2 DVD commentary for the episode "Simpson and Delilah" [DVD]. 20th Century Fox. Smithers was once shown to be a baby when Homer Simpson was 12 years old, [3] while in other episodes he was in grade school [4] and high school at the same time as Homer. [5] [6] It's possible that the corpse of Waylon Smithers, Sr., who died when his son was 4 months old, was never found for at least 12 years, but if that were the case and reality were to apply, the corpse would be much more decayed than it appeared to be, and possibly nothing but dust, as Waylon Sr. died of radiation poisoning, which causes corpses to decay faster than normal.

He was once, however, made the CEO of the Nuclear Power Plant in Burns' stead when Mr. Burns was arrested for stealing paintings from an art museum, a position that is arguably better than vice president, although he hints that he didn't want the job. He initially tried to be an employee-friendly boss, but after overhearing a conversation between Lenny, Carl, and Homer while meeting at Moe's Tavern that revealed that they were abusing his employee-friendly nature to in essence goof off, he became a worse CEO than Mr. Burns (even going as far as to release wolverines in the house instead of hounds). He eventually gave up on the position willingly after Burns was released by Lenny, Carl, and Homer. [20]Smithers's relationship with Mr. Burns has long been a running joke on The Simpsons. Smithers is an obedient and sycophant assistant to Mr. Burns. There have often been strong hints about Smithers's true feelings for his boss, with one of the earliest references being in the season one episode " The Telltale Head". [38] Smithers's sexual orientation has often come into question, with some fans claiming he is a "Burns-sexual" and only attracted to his boss, while others maintain that he is obviously gay. During the Bill Oakley/ Josh Weinstein era, they still tried to keep his sexuality difficult to pigeon-hole. There was debate among the writers about his orientation. Al Jean, who thinks of Smithers as being a "Burns-sexual", [40] felt that had Mr. Burns been a woman, then Smithers would not be gay. [45] David Silverman, a former supervising director has said, "[Smithers] seems to be focused on one particular human, as opposed to anything beyond that. [Rather than being gay], he's sort of 'Burns-sexual'". Smithers hinted at possibly being transgender when Marge was selling prescription medication at a garage sale and he bought bottles of estrogen for "a friend...who's trapped in the body of another friend." [60]