I'm on record as loving this show way more than I should. For years I curated (okay, 90% wrote) a loving episode guide which included such goodies as the Shawn Cuteness Chart.
Boy Meets World is stealth funny: a wacky, increasingly surreal comedy in the sheep's clothing of a bland, gentle family sitcom. But the gentleness is still there. It's that edge of oddness and occasional moments of legitimate laugh-out-loud humor that make the show one of the most watchable in history. At least for me. It is very much a comfort show.
The challenge in identifying key episodes of Boy Meets World is that the best and funniest episodes often are not the ones in which plot-central changes happen. The show seems like it wants the Cory and Topanga romance to be its central story, but if I were to list all of the episodes in which Cory and Topanga broke up or got back together, we'd be here all day. More interesting is the character development of Shawn, whose easy flirtations with the ladies mask a troubled family life. Unintentionally interesting is the arc of Eric, who starts out a standard cool big brother type, quickly becomes impossibly stupid, and winds up carrying the most bizarre, different-plane-of-reality storylines in the show.
Fairly Arbitrarily Selected Key Episodes
2.22 "Career Day" & 2.23 "Home": In the season 2 finale, the "Shawn is abandoned by his family" storyline takes off, as Shawn stays with Cory's family indefinitely, revealing the differences between his lifestyle and theirs. Am I really going to declare such a Cory-light two-parter the first "Key Episode"? Yes. Yes, I will. Look, it's the first major, memorable, multi-episode storyline, other than the Cory/Topanga romance, which hasn't really gotten off the ground yet. To get a feel for what the show is typically like, maybe watch any random episode from season 2 before this; see "Bonus Episodes" for suggestions.
4.2 "Hair Today, Goon Tomorrow": Topanga gets a haircut. Trust me. Trust me. Trust me. It's important.
5.23 "Things Change" & 5.24 "Graduation": The kids graduate and make big decisions about what to do after, as Topanga considers leaving Cory for Yale; Shawn considers going to work instead of college; and change-averse Cory is disturbed by everything. My theory, developed just from picking out these key episodes, is that this is a show about endurance vs. change, specifically the power of friendship, family, and true love to withstand changes in age/time of life, personality, setting, and genre. I'm not sure I agree with this thesis, but I like it, in the context of the show. We might progress from gentle sitcom to farcical comedy; from elementary school show to college show; from Weird Topanga to Smart Topanga; from Cool Eric to Dumb Eric; from Bad Boy Shawn to Poet Shawn; from childhood to adulthood; but the heart of the show, specifically the relationships between Cory, Topanga, and Shawn (and to a lesser extent: Eric and Mr. Feeny) never really change. It's comforting. And that is what this show is about.
Unnecessarily Long List of Bonus Episodes
Boy Meets World has a lot of mediocre episodes. You can kind of watch any of them and get a decent feel for the show, particularly if you stick to the golden age of seasons 2 through 5. The episodes listed here are either above average in quality or advance a memorable plot arc.
1.4 "Cory's Alternative Friends": In her first appearance--as one of the "weird nerds"--Topanga, apparently meant to be a one-shot throwaway character, gives Cory his first kiss. I'm not a big fan of season 1, which adheres much more strongly to the gentle-family-sitcom mold than the rest of the series, but this episode has interesting historical value.
2.7 "Wake Up, Little Cory": Typical of season 2, the plot comes from a story--in this case, "Much Ado About Nothing"--as Cory and Topanga are rumored to have slept together. It's a surprisingly adult rumor for a mainstream show about seventh-graders, even though everything is handled euphemistically, and it mildly advances the Cory and Topanga storyline, which is mostly dormant in season 2.
2.11 "The Beard": Shawn can't decide between two girls, so he asks Cory to date one for safekeeping. A fairly typical, maybe slightly above average season 2 episode, which confirms Cory's role as nonthreatening goober and Shawn's as seventh-grade Casanova.
2.12 "Turnaround": This is just a classic episode of any high school sitcom, I think. Cory and Shawn give Cory's date for the Turnaround Dance a makeover, and she turns from nerd to hot and becomes too good for Cory. I'm always referencing this episode, at least, the part where Shawn is always up to the moment on Cory's romantic mishaps because "I'm tapped into the Girls Network."
3.1 "My Best Friend's Girl": Cory finally asks out Topanga out of spite after Shawn inspires his jealousy by asking her out himself.
3.9 "The Last Temptation of Cory": The first (but not last) official Cory and Topanga breakup occurs when they both secretly flirt with other people who, of course, turn out to be each other.
3.15 "The Heart is a Lonely Hunter": For the first time, Shawn's tender feelings are involved in one of his love affairs. Guest-starring Larisa Oleynik.
3.20 "I Never Sang For My Legal Guardian": Just as Shawn is wavering about whether to make his arrangement with Mr. Turner official, his father talks him into coming back home, mostly concluding the "homeless Shawn" subplot.
4.11 "An Affair to Forget": Shawn's girlfriend wants him to drop Cory, forcing him to decide what's more important to him--romance or friendship.
4.15 "Chick Like Me": The classic "Shawn in drag" episode.
4.16 "A Long Walk to Pittsburgh Part 1" & 4.17 "A Long Walk to Pittsburgh Part 2": Topanga's family moves away, a major and memorable plot development which many kids who grew up on this show might be surprised to realize was resolved in a two-part episode. She wasn't gone for more than an episode. I know, it's a mind eff.
5.1 "Brothers": In a contrived plot twist, Eric's new roommate Jack (Matthew Lawrence) is Shawn's long-lost half-brother.
5.3 "It's Not You... It's Me": Cory and Shawn's relationship faces its biggest trial yet when Shawn picks a fight in order to detach, assuming Cory will get into a better college than he will. Not necessarily a key episode, but one of my favorites.
5.7 "I Love You, Donna Karan": Shawn falls in love with a girl based on her purse. The first episode featuring Shawn's first longterm girlfriend, Angela (Trina McGee-Davis).
5.13 "The Eskimo": Mr. Feeny assigns Cory, Shawn, and Topanga apparently impossible tasks to shake them out of senior slump. A solid episode with important character moments for all three.
5.14 "Heartbreak Cory": Cory kisses another girl at a ski lodge, ushering in the biggest Cory and Topanga estrangement plot of the series.
5.17 "And Then There Was Shawn": A horror movie parody I'm only recommending because it was kind of surprisingly hilarious.
5.19 "Eric Hollywood": Eric becomes an actor and goes on the set of a parody version of the show. One of the show's sillier episodes, but also one of the funniest; you really feel like you get a sense of the behind-the-scenes dynamic through the send-up.
5.20 "Starry Night" & 5.21 "Honesty Night": Cory and Topanga reaffirm their love for what one hopes is the last time.
5.22 "Promises, Prom-ises": I love a sex on prom night episode called "Promises Promises." Classic 90s.
6.3 "Ain't College Great?": In the slightly rebooted, college-years version of the series, Cory worries about failing out, and Eric remakes himself into a "sensitive guy" to flirt with his new girl roommate (Maitland Ward).
6.9 "Poetic License: An Ode to Holden Caulfield": College Shawn is a poet. While he's quite different from his season 1 or 5 self, it feels like a natural progression, and perhaps a case of the character becoming more like the actor.
7.7 "It's About Time": Cory and Topanga's wedding--a fairly hyped television event, if I recall correctly--has its fair share of humorous disasters, and ends, fittingly, with Shawn standing at the altar between the two of them.
7.23 "Brave New World Part 2": (I'm not including part 1 because it's a clip show.) The sentimental final episode of the series, notable for the oddly satisfying ending in which Topanga and Cory move to New York City for Topanga's job--and Shawn goes with them. Confirms my belief that the core of the show is about Shawn's search for a family.
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