In its current 34th season, The Simpsons has introduced a bunch of new characters, like Jesse, a hunky parody of Peloton instructors, and a fourth-wall-breaking hacker voiced by guest star Anna Faris. From Krusty the Clown to Ralph Wiggum to Ned Flanders to Moe Szyslak, many fan-favorite Simpsons characters have been around since the very first season.
But some of the show’s most beloved characters, like Fat Tony, Troy McClure, Mayor Quimby, Groundskeeper Willie, and Comic Book Guy, didn’t join the ensemble until later seasons.
10 Mayor Quimby
The long-standing mayor of Springfield – Joseph Fitzgerald O’Malley Fitzpatrick O'Donnell The Edge Quimby, also known by his nickname “Diamond Joe” – made his first on-screen appearance in the season 2 premiere, “Bart Gets an ‘F’.” Quimby has somehow managed to stay in office for decades despite having all his corruption out in the open.
Quimby is a composite caricature of various members of the Kennedy family, including President John F. Kennedy and U.S. Senator Ted Kennedy, and Dan Castellaneta nails the impression.
9 Professor Frink
“Professor Frink, Professor Frink, he’ll make you laugh, he’ll make you think.” Long before he was cut off in the middle of debuting his self-penned theme song in the season 7 anthology episode “22 Short Films About Springfield,” Professor Frink first appeared in season 2’s “Old Money.”
Inspired by Jerry Lewis’ iconic turn as Julius Kelp, the original Nutty Professor, Frink is the resident Springfieldian brainiac who sets up all the show’s sci-fi storylines.
8 Groundskeeper Willie
From Principal Skinner to Mrs. Krabappel, many hilarious employees of Springfield Elementary made their debut in season 1 of The Simpsons. But Groundskeeper Willie didn’t show up until season 2’s “Principal Charming,” the episode in which Skinner falls for Aunt Patty.
Known for his short temper, his Scottish pride, and his loyalty to Skinner, Willie always gets plenty of laughs whenever he pops up in an episode of The Simpsons.
7 Lionel Hutz
Lionel Hutz first appeared in season 2’s “Bart Gets Hit by a Car” when the Simpsons hired him to represent Bart against Mr. Burns in court. Played hilariously by the late, great Phil Hartman, Hutz is a fraudulent ambulance chaser who figures out his defense strategies by watching TV legal procedurals with the sound off in bars.
Hutz is the polar opposite of Springfield’s other most famous attorney, the Blue-Haired Lawyer. Rather than using unscrupulous methods to get rich, guilty clients off the hook, Hutz’s absurd incompetence makes him lose what should be open-and-shut cases.
6 Comic Book Guy
Comic Book Guy first appeared in season 2’s “Three Men and a Comic Book,” and – as a spot-on spoof of every pop culture fan with high standards – the character has only gotten more relevant over time. He enjoys declaring things to be the worst ever. After a screening of Cosmic Wars: The Gathering Shadow, Comic Book Guy says, “Worst Cosmic Wars ever! I will only see it three more times... today.”
The writers sometimes use Comic Book Guy’s pop culture fandom for a meta commentary on their own show, often declaring a given Simpsons episode to be the “worst episode ever!”
5 Dr. Hibbert
Although Homer gets himself into life-threatening scrapes and injuries on a daily basis, the Simpson family’s physician Dr. Hibbert was nowhere to be seen in the show’s first season. Instead, the chuckling doctor first appeared in season 2’s “Bart the Daredevil.”
Inspired by a local stuntman, Bart decided to attempt dangerous feats for the entertainment of his classmates. Dr. Hibbert, of course, advised against this – but he punctuated that advice with his signature laughter.
4 Mona Simpson
While Homer’s dad Abe has been featured prominently since the beginning of The Simpsons’ run, his absentee mother Mona has only appeared in the occasional episode. Mona briefly showed up in a flashback in season 2’s “Oh Brother, Where Art Thou?,” marking her first on-screen appearance.
The character wouldn’t make her proper debut, brought to life by a beautiful guest performance by Glenn Close, until she reconnected with Homer and met Marge and the kids in season 7’s “Mother Simpson.” From then on, she was a Simpsons icon.
3 Hans Moleman
Although a character who looks like him (without the glasses) can be seen sleeping in a movie theater in one of the original Tracey Ullman shorts, the Hans Moleman that fans know and love first appeared in season 2’s “Principal Charming,” although his driver’s license identified him as “Ralph Melish.”
Moleman has been theorized to be part of a race of underground clones trying and failing to invade the surface world. Either that, or he’s just the unluckiest man in Springfield.
2 Fat Tony
Anthony “Fat Tony” D’Amico first appeared in season 3’s “Bart the Murderer,” in which he hired Bart to work as an errand boy, à la Henry Hill in Goodfellas. Fat Tony might be a fearsome mob boss who robs, intimidates, and kills people for a living, but he’s also oddly lovable.
Whether he’s relating to Garfield or getting an earful from his wife about the whereabouts of the pretzel money, Fat Tony is always hilariously relatable in spite of his illicit line of work.
1 Troy McClure
Lionel Hutz isn’t the only fan-favorite Simpsons character voiced by the late Phil Hartman. Hartman also provided the voice of Troy McClure, who first appeared in season 2’s “Homer vs. Lisa and the 8th Commandment.” McClure is a Z-list actor seen in schlocky low-budget movies, tacky infomercials, and wildly inaccurate educational films.
The writers always had a field day coming up with fake movie titles to finish Troy’s introductory catchphrase: “Hi, I’m Troy McClure, you may remember me from such films as...”
Source:gamerant.com