“Simpsons Roasting On An Open Fire” – Original Air Date: December 17, 1989
Yes, it took only the first episode for Homer to end up in a new job. Although, unlike the wackier later episodes, this was a strictly down-to-earth affair, in which Homer takes on a part-time job as a Mall Santa to make some extra cash when he doesn’t get his Christmas bonus, and Marge spends all the family’s extra money having Bart’s tattoo removed. Homer’s miserable labor earns him a mere $13, but chance is in his favor. While his attempts to win big at the dog track fall through, he lucks out when Santa’s Little Helper — the last place dog that Homer bet on — jumps into Bart’s lap, and the family ends up having a merry Christmas after all.
“Lisa’s Pony” – Original Air Date: November 7, 1991
Another episode in which Homer has to take on a second job. This time, he suffers through an exhausting gig at the Kwik-E-Mart to help pay the expenses of the pony he bought for Lisa after he couldn’t deliver a saxophone reed to her recital on time. Lisa loves her pony, but when she sees all the work Homer is going through (he sleeps about five minute a night), she does the only sensible thing and gives it up. This episode brings Homer and Lisa much closer together and plus, and we get the brilliant sequence of Homer falling into “Slumberland” while driving home from work.
“Deep Space Homer” – Original Air Date: February 24, 1994
A favorite episode of many, and for good reason. This is one of the most ambitious ideas the Simpsons writers ever attempted, and the fact that they managed to make an episode where Homer Simpson is blasted into outer space seem fairly realistic is a testament to how great this show was in its prime. Homer is selected for the space program because of his appeal as an “average man,” and little consideration is given to the fact that sending him into space is incredibly dangerous (those NASA folks are just after the TV ratings). Luckily, he makes it out alive thanks to that glorious Inanimate Carbon Rod. In Rod We Trust!
“Homie The Clown” – Original Air Date: February 12, 1995
It’s the first day of the month, new billboard day! So, if you’re driving around today and see a billboard advertising a brand new clown college, you can hardly be blamed if you’re just as powerless against it as Homer is in this episode. Homer is a natural choice to be an imitation Krusty The Klown, because as you may have noticed, Krusty is basically Homer with makeup, which this episode makes quite clear. Homer is goofy enough to handle some of Krusty’s duties, but he’s too tired to handle Milhouse’s birthday, and his treatment of the Krusty Burglar is downright disturbing (“Stop! Stop! He’s already dead!”). Thankfully, Homer makes the right decision, and decides to leave the clowning business to all the other clowns in the clowning business.
“Homer Vs. Patty and Selma” Original Air Date: February 26, 1995
Patty and Selma’s hatred of Homer has been a part of The Simpsons from the very beginning (no, seriously, it comes up in the first scene of the first episode), so when they get a chance to lord something over Homer, they seize the opportunity. When Homer squanders the family’s money by not selling his pumpkin stocks before Halloween, Patty and Selma offer him a loan, but they annoy him about it at every step, and even spill the beans to Marge. Homer’s means of making extra money is taking a second job as a limo driver. Unfortunately, he gets busted for not having a Chauffeur’s License, and the only way to get one is from… Patty and Selma. Luckily, they get caught smoking on the job, and when Homer takes the blame for them, they have no choice but to forgive the debt. So, Patty and Selma realize that Homer is actually a decent guy, and Homer got to meet Mel Brooks. Everybody wins!