Because this show is currently on, all Key Episodes are provisional. While I do think the show's best days are behind it, I suspect that this is a show where the ending has already been planned, and one or more episodes in the endgame will end up being key.
This is actually show where I have done the "key episodes" thing in practice--picking out episodes to try to get people hooked. I thought you might like to benefit from my wisdom.
Top 3 Key Episodes
1.3 "Sweet Taste of Liberty": Dragged along on a crazy night when all he wants to do is stick to his familiar rut, Ted (Josh Radnor) wonders why he hangs out with immature Barney (Neil Patrick Harris), until he realizes Barney's adventures constitute all his best stories. I start with this one when showing it to new people instead of the two-part opener in which Ted meets Robin (Cobie Smulders) and decides she is the one for him. Although the Ted story is more central, arguably, to the main plot--setting up his "hopeless romantic" personality and his obsessive desire for a mate--it's a cringeworthy storyline which tends to put people off more than it draws them in. Anyway, the writers themselves seem more interested in Barney these days, and I don't think it would be too far off to suggest that the Ted and Barney friendship is more central to the heart of the show than Ted's MacGuffin-like quest for love.
2.9 "Slap Bet": I can't tell if I'm confusing favorite episode for key episode here, but I do think this is an episode which originates the most well-known references which people might make to HIMYM, so it's important. The Slap Bet between Barney and Marshall (Freaks and Geeks alum Jason Segel) becomes a recurring storyline on the show; Robin's backstory is revealed; Ted and Robin click as a good couple in this episode, and everything is just on, firing on all cylinders. The jokes are great. If you only see one, see this one.
2.22 "Something Blue" The season 2 finale--Lily (Alyson Hannigan) and Marshall's wedding--is a good example of HIMYM at its building-storyling playing-with-timelines best, as Robin and Ted's "big news" keeps getting cut off by wedding antics.
Bonus Episodes
1.8 "The Duel": Ted worries that Marshall and Lily will take over the apartment when they get married, leading to a sword duel with Marshall. It's a fun episode that takes on one of the central issues of the show--Ted and Marshall's relationship and his fear that Marshall and Lily are maturing faster than he is.
1.14 "Zip, Zip, Zip": Ted goes on a typical romantic quest to find a girl he met at a wedding the night before, while Robin wingmans Barney, setting up her most badass personality traits and the manly chemistry between the two of them.
1.15 "Game Night": Barney's backstory is revealed.
2.10 "Single Stamina": We meet Barney's brother (Wayne Brady), get some fun night-out hijinks, get a deeper understanding of Barney's attitudes toward marriage and kids, and top it off with a cool flash-forward hint-at-what's-to-come in classic HIMYM style.
2.16 "Stuff": A medium Ted and Robin plot (helped by a fantasy sequence in which Robin's dogs are played by puppy-like men) and a delightful Barney plot in which he tests Lily's assertion that friends should support each other unconditionally by putting on a dreadful one-man play.
2.17 "Arrivederci, Fiero": A series of flashbacks about what Marshall's car meant to each character reveals a number of hilarious backstory elements, including Pretentious College Ted.
2.20 "Showdown": Nice buildup to the Lily/Marshall wedding and some tender romance between them, but what makes this episode important is Barney's belief that Bob Barker of The Price is Right is his father. Introduces daddy issues we'll see explored in later episodes.
3.8 "Spoiler Alert": The group spoils each other by revealing annoying traits they had all been able to ignore about each other until now, leading to a huge argument which is undercut by Marshall finding out his bar results. This is a good example of several things the show does well--goofy, trivial problems which mask real, deep conflict, and real earned tenderness. A group love story.
3.9 "Slapsgiving": While it feels a little like this holiday episode is trying to rehash the popularity of "Slap Bet," it's also a pretty good episode, focusing on the post-breakup relationship between Robin and Ted and including one of my favorite joke sequences as Ted riffs on the appetizers.
3.16 "Sandcastles in the Sand": The group interact with people from their past who make them act like past versions of themselves; more Robin backstory; and an important relationship milestone.
4.21 "The Three Days Rule": One of my favorite post-golden-age episodes, if only for its slash content. Trying to save Ted from over-texting a girl he's just met, Barney and Marshall text him posing as her.
5.12 "Girls Vs. Suits": Barney has to choose between his two great loves. A slightly above average episode jazzed up by a big-budget musical number.
6.14 "Last Words": An island of real emotional heart in a somewhat silly season, the friends try to help Marshall deal with the death of his father.
6.19 "Legendaddy": Continuing the daddy issues theme of season 6, Barney spends time with the man he's just discovered is his real father (John Lithgow) and is disappointed that he is a suburban driving instructor and not a badass rock star.
7.12 "Symphony of Illumination": In a cool concept episode, Robin, fresh from a pregnancy scare, tells a story to her own future children.
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