Today marks three years since the finale of How I Met Your Mother. Like a lot of fans, even all this time later, I’m still torn on my feelings about that final episode and how Craig Thomas and Carter Bays ended things. However complicated my emotions about the ending, though, there’s no denying the impact HIMYM had on my life, inspiring my love of long-term storytelling and serving as a cornerstone of my own sense of humor.
I was a freshman when the show premiered, and it remained one of my favorite pieces of entertainment throughout high school and college. The show was appointment viewing for me even in the rough years, and I’ve rewatched episodes again and again on DVD, Netflix, and reruns. So, with the show now three years gone, it felt like as good a time as any to look back on the best episodes of the show.
Rather than a straight top episode list, though, I’ve instead looked at all nine years of the show and selected the best episode of each season. Further, it won’t just be the funniest or most emotional episodes, but the ones that best represents their respective seasons as a whole. As such, let’s turn the clock back to 2005 and remember, remember the greatest episodes of How I Met Your Mother.
Season 1: “The Pineapple Incident”
Look back at the first season of any long-running show, and there’s a good chance you’ll find something unrecognizable from what it ended up. This comes from a mix of good – character development, running jokes – and bad – character broadening, running jokes run into the ground – elements; but at the most base level, the first season of a show is formative, with actors and writers alike getting to know the characters and who they are.
What’s impressive about How I Met Your Mother is how quickly it gets a handle on its group of friends, and how quickly it realized just how creative it wanted to be with its storytelling. Telling the out-of-order, flashback-heavy story of one drunken night in Ted Mosby’s life, “The Pineapple Incident” is the young series at its most ambitious. It layers in a number of great bits of foreshadowing and twist reveals, working as an early example of the sort of season- and series-long mysteries the show would work with time and again.
It also does a good job of highlighting each character’s role within the group, from Ted as the hopeless romantic far too often stuck in his own head to Barney as a fun-loving agent of chaos. If anyone is thinly drawn, it’s Robin, but that’s a sign of the first season, with her place as the new friend/outsider still keeping her at an arm’s length. Add in that it’s also one of the first season’s funniest episodes – Ted on fire, drunken karaoke, and Carl the vampire bartender are all classic moments – and you have an all-around winner that no doubt won over plenty of early viewers.
Runners-Up: “Pilot,” “Okay Awesome,” “Drumroll, Please,” “Come On”
Season 2: “Slap Bet”
Not every episode on this list is going to be the most obvious choice, but to argue anything other than “Slap Bet” belongs in the top spot here would be ridiculous. Beyond just the second season, this episode is one of the funniest episodes of the show period, not to mention important for setting up the show’s two biggest recurring elements: the eponymous Slap Bet and Robin’s teen pop star alter-ego, Robin Sparkles.
Really, what’s there to say about this episode that hasn’t already? Comically, it has something for everyone, from the physical humor, to sight gags, to a gaggle of slap-based wordplay. It gives the show its first – arguably best – major musical number with “Let’s Go to the Mall”. And narratively, it’s primary focus is on the relationship between Ted and Robin, the main focus of the entire second season. It’s just a classic episode of the series, and arguably the best half-hour it ever produced from a comedic standpoint.
All that said, it would probably be better served cutting out that transphobic “What if Robin’s a dude?” joke. Could say that for a few episodes, sadly.
Runners-Up: “Ted Mosby: Architect,” “Arrivederci, Fiero,” “Bachelor Party”
Season 3: “Ten Sessions”
Without question, there are funnier third season episodes than “Ten Sessions”; runners-up “Third Wheel” and “Spoiler Alert” likely vie for the top spot in that regard. And in terms of narrative significance, “Third Wheel” also works well, with much of season three dealing with what it’s like when Ted goes full bachelor and embraces his inner Barney. However, the true lesson Ted learns in season three is that however much fun all the meaningless sex and dating might seem in the moment, they’re not leaving him truly fulfilled; and, in the case of “No Tomorrow”, they’re making him a worse person for it. In fact, by season’s end, he basically calls Barney out for the same crappy behavior, leading to an episodes-long falling out between the two.
The turn for Ted starts in “No Tomorrow,” but it all comes to a head in “Ten Sessions” when he meets his future fiancée Stella. Again, it’s not the funniest episode, but “Ten Sessions” is all about Ted remembering the romantic he really is as he finds himself falling for Stella during his ten weeks of tattoo removal. By the end, he learns that Stella has a daughter, and that she barely has any time to date.
The episode then ends with, for my money, the perfect show of Ted Mosby’s romanticism, as he enlists his friends to put on a two-minute date with Stella, drawing from their conversations together to give her a midday burst of romance just to show how much he’s enjoyed his time with her. And while it could be seen purely as an attempt to woo her – it certainly is to some extent – his willingness to ask for a kiss, to leave the ball of their future fully in Stella’s court, show that he’s not as obsessed or trying as hard as he did with Stella. For me, this is the best version of Ted, before he was lost down the rabbit hole of self-loathing and self-sabotage of later seasons. For that reason, “Ten Sessions” is also the third season’s best episode.
Runners-Up: “Third Wheel,” “Dowisetrepla,” “Spoiler Alert,” “No Tomorrow,” “Sandcastles in the Sand”
Season 4: “The Best Burger in New York”
On sheer laughs, “The Naked Man” might actually be the funnier episode, but “The Best Burger in New York” comes close while also being an early example of the fourth season’s expanding focus on characters beyond Ted. Make no mistake, How I Met Your Mother has been an ensemble show from the beginning, and the other characters have had storylines along the way. However, the fourth year is where the show really starts to shift from focusing as intensely on Ted’s romantic life, allowing for the other four leads to take the spotlight in new ways. Most importantly, this is the season where Ted fully takes a back seat to the other characters, with episodes fully devoted to one of the other cast members.
In many ways, “Best Burger” is the be-all, end-all Marshall episode. At its heart, it’s an episode about Marshall both remembering his roots and fearing for his future. He no longer has the safety of law school to cushion him as he dreams of working for the NRDC. Instead, he now has to worry about student loans, apartment payments, and credit card debts, which means taking a corporate job that’s no better to him than selling out. So, like anyone faced with a major life change, he seeks shelter in nostalgia and the hunt for a legendary burger.
On top of the character development, it’s also a funny episode that reminds the audience just how much Marshall loves good food, from his poetic waxing about the perfect burger to the maniacal lengths he’s gone to trying to find it once again. Throw in Robin’s struggles to get some food in her mouth, a solid Regis Philbin guest spot, and the numerous examples of Marshall’s post-college malaise, and you’ve got a winner.
Runners-Up: “Woooo!” “The Naked Man,” “Three Days of Snow,” “The Stinsons”
Season 5: “Perfect Week”
When the fifth season first premiered, I was pretty ambivalent to it, mainly because of how invested I was in the mystery of the Mother. More than any other season, there’s almost no forward momentum on that front to be found this year, which was frustrating at the time. Now, however, I can see that the secret success of season five is that it offers up some of the show’s funniest takes on different dating tropes, as well as a run of all-around fantastic standalone episodes.
Not surprisingly, then, some of the season’s funniest episodes focus on resident playboy Barney Stinson, so it only feels right to give this year’s honors to one such outing. And while “The Playbook” offers up plenty of gambits, hoodwinks, and flimflams, “Perfect Week” is the more successful episode because it actually gives some motivation for Barney’s constant sleeping around beyond just doing it to do it. As most people do when faced with failure in one area of their life – possibly being fired in this case – Barney puts all his energy into another, attempting to sleep with a different woman each night for seven days: the perfect week.
It’s as ludicrous as any episode centered on Barney tends to be, but it works because his friends – well, Lily – realize what’s really going on and try to help him work through his fears. Moreover, it’s just damn funny, with the show offering a ridiculous amount of baseball metaphors for sex and dating that all manage to knock it out of the park. In a season full of frivolous, but joyful episodes, “Perfect Week” lives up to its title well.
Runners-Up: “Definitions,” “The Playbook,” “Girls Versus Suits,” “Zoo or False”
Season 6: “Big Days”
While season five was a loose, silly season, the show cranked the serialization dial up to 11 with its sixth year. A narratively self-contained arc for Ted that also manages to set-up the mysteries of the show’s endgame, season six is an interesting experiment that doesn’t always quite work, but is still entertaining more often than not.
And with such a heavily serialized season, it’s perhaps not a surprise that the first episode stands as one of the best, setting up a number of plot points and phrases – sundresses, “new is always better” – that would recur throughout the season. It’s a fun bottle episode taking place almost entirely at the bar, with the show relying entirely on the strength of the core five characters to zip along. And, with a single flash-forward, the show gives us the first look at the day Ted would meet the Mother, the day of a wedding.
It’s not the biggest episode ever, I’ll admit, and perhaps the emotional high point of “Last Words” would be a more appropriate pick for some readers. However, when I think back on how season six kicked the show back into gear after a meandering fifth season, it all comes back to the strength and ease of the season premiere.
Runners-Up: “Natural History,” “Blitzgiving,” “Last Words,” “Oh Honey”
Season 7: “Ducky Tie”
While I have a deep love for How I Met Your Mother as a whole, I’m more than willing to admit that seasons seven and eight are rough. The show was fairly long in the tooth at this point, but its ongoing success meant that CBS wanted to keep renewing it and extend the mystery. What did this mean for viewers? A whole lot of teasing out of the storyline, with plenty of potential promised, but never delivered on. So, there’s perhaps no better episode to represent the seventh season than this early outing that featured the biggest of all possible developments: the return of Victoria.
Ted’s season one love interest – and the woman who would’ve been the mother had the show been cancelled early on – still stands for many as Ted’s best on-screen romance, and the tease of her return at the end of the previous episode meant that “The Ducky Tie” had a lot of hype to live up to. Fortunately, it does just that, featuring an easy reunion between Ted and Victoria, with the story of their night out together told in classic, flashback-heavy HIMYM form. The narrative even manages to tease the unresolved weirdness between Ted, Robin, and Barney, and just before the Barney/Robin dynamic became exhausting to boot.
And as I’ve noted time and again with this list, it’s also a phenomenally funny episode, with Barney’s hibachi con serving as a great present-day source of laughs as the drama plays out in the past. It was an episode that managed to ramp up the promise of another great year for the show, only for the seventh season to fail to deliver. Of course, things only get worse in our next entry.
Runners-Up: “Tick Tick Tick…” “Symphony of Illumination,” “No Pressure,” “Trilogy Time”
Season 8: “The Time Travelers”
The eighth season of How I Met Your Mother, for lack of kinder words, is kind of a garbage fire. The first half of the season is a string of miserable, unfunny episodes featuring the destruction of once-likable characters – poor Victoria… – and a nonsensical proposal plot from Barney. The second half fares a bit better, but it’s clear that the creators were running out of steam. Honestly, to truly embody this season, I’d need to pick a low-point episode like “The Pre-Nup” or “The Autumn of Break-Ups”.
Instead, there’s a better pick in “The Time Travelers,” an episode that manages to put the season in a completely different context and get to the heart of the problem: eight years on from when we met him, Ted has become a lonely, miserable person. He’s someone who lives in the past, thinking back on happier times with his friends, stunted and alone as they all move on without him. It’s an episode that starts as bizarre as anything the show has done before delving into deeper, harder truths about its main character.
In a way, it’s a recognition from the creative team of just how sad Ted and how aimless the show have been. At the end, Future Ted imagines going back to that night, 45 days before he would meet the love of his life, just so he could find her all the sooner. It’s the first true hint of the dark ending in store for the Mother, but it also sells just how exhausted Ted was with his personal life at that point: ditto the audience.
Runners-Up: “The Ashtray,” “Weekend at Barney’s,” “The Bro Mitzvah,” “Something New”
Season 9: “How Your Mother Met Me”
Take away the “all in one weekend” gimmick, the cruel twist ending, and all of the ludicrous Barney/Robin drama in the eleventh hour. At the end of the day, the ninth season is about one thing, and one thing only: introducing and making us care about the Mother. And while Cristin Milioti’s absolutely charming performance had already been winning hearts for half-a-season, it’s the masterpiece outing of “How Your Mother Met Me” that solidified her as a truly fantastic character independent of Ted Mosby.
Whereas Ted had spent the past eight years looking for the love of his life, Tracy McConnell was convinced she’d already found and lost hers. The same night that Ted first saw Robin, Tracy learned that her boyfriend Max had died, and the next few years of her life were withdrawn and lonely. Over the course of the episode, we not only learn what Tracy had been up to during the series, but we see her come to terms with the greatest loss of her life, watch her struggle to love again. In the process, we absolutely fall in love with the character.
Again, it all comes down to how much warmth, humor, and sincerity Milioti imbues the character with. She’s instantly likable and relatable, quickly building on her few appearances earlier in the season to make Tracy a fully realized individual. From watching her ask Max for permission to move on to her sorrowful performance of “La Vie en Rose”, there isn’t a moment in this episode where your heart isn’t breaking for this character. We want the best for her, and it makes us just as excited to see her meet Ted as the other way around. Like “Slap Bet”, it’s not just a stellar outing for the season, but an all-time high point for How I Met Your Mother as a whole.
Runners-Up: “No Questions Asked,” “Bass Player Wanted,” “Slapsgiving 3,” “Gary Blauman”
And that’s our list! Which episodes were we crazy to include, and which should’ve obviously made the cut? Let us know in the comments!