9. Season 8
Ugh, this show got bad towards the end of its run. There was a lot wrong with it — unfunny stories, character development ranging from goofy to garish, narrative spinning wheels — but the most troubling thing about the show in its wretched penultimate season was how little it seemed to care about its characters. Robin — once a unique, strong character depicting a side of feminine independence rarely seen in media — and Lily alternated between bitchy and horny. The male characters were not much better off, as Ted was glorified for being in a toxic but sexy relationship and Barney became engaged to Robin in about as implausible and deceitful a way as imaginable. There was maybe one good, clever episode (“The Time Travelers”) as HIMYM crashed and burned.
8. Season 7
In the midst of a tailspin, the jokes became unfunny and the stories became boring. But there’s one thing that Season 7 did right, enough to buoy it at least one tier above the season that followed it: It focused its dramatic and romantic stories around Neil Patrick Harris, easily the best actor of the regulars. Sure, the writing wasn’t always there — the inevitable path to Robin and Barney getting together was full of awkward starts and stops, plus general ineptitude in handling Ted and Robin’s baggage. But NPH is a treasure, and he carried the show like ’07 LeBron. Another plus: Allison Williams reappeared as Victoria. She’s always a bright spot, even when this show is at its darkness.
7. Season 5
In retrospect, HIMYM‘s downfall was sharp and ugly. The show thrived on such a specific meditation on growing old and experience romance, such a specific crossroads for the characters, it was bound to sour. As the characters became full-fledged adults, their most potent stories stalled out. The fact that the jokes got less funny hurt, too. It was still a decent show at this point, but given that its peak was basically Sandy Koufax, a redefining force of sitcom energy and creativity, “decent” is a damn shame for HIMYM.
6. Season 9
Listen, I know that the final season of How I Met Your Mother is not strictly good television. (And I’m not even going to touch the finale, perhaps the most divisive episode of television since Lost.) But it was something that the show hadn’t been in years: interesting. By forcing a tight structure, focusing on long-overdue payoffs, and striving for meticulous fan service, the show attempted to steamroll its own ineptitude with ambition and creativity. While there were misfires, there were also some fantastic highs (like this). Mostly, it was just exhilirating watching the show swing for the fences, batting average be damned.
5. Season 6
The show’s sixth season continued the shows downward stumble in the overall craft department. But it redeemed itself with an extremely solid backbone of two of the show’s best dramatic stories: Barney finding his father, and Marshall losing his. It allowed both Jason Segel and NPH to show their dramatic chops and gave noteworthy, game-changing arcs to the show at a relatively late stage in the game. Sure, “The Exploding Meatball Sub” is a fart of an episode, and not the only one, but when “Legendaddy” is this good and “Oh Honey” is this warm, can you not forgive the occasional miss?
4. Season 3
Frankly, you can arrange your preference of the first four seasons of HIMYM in any order you please, and I won’t quibble too much. Season 3 has some of the show’s best episodes: “The Platinum Rule” is a great primer on the show’s best quirks, while “How I Met Everyone Else” steeps the show’s characters in hilarious backstory. But there are also some of my least favorite early HIMYM stories here: the show’s first stab at RoBarn, Marshall’s corporate job, and Lily’s credit score.
3. Season 4
Surprisingly solid for four seasons into an ostensibly novelty sitcom, HIMYM excels in its fourth outing. Granted, it’s not all sunshine: There’s too much Stella and Stella fallout. But, damn, those highlights: “Three Days of Snow” is brilliantly structured; “The Naked Man” is built around one of the show’s funniest gags ever; and “Best Burger in New York” provides perhaps the show’s most brilliant two minutes. Best of all, my personal favorite episode of the entire series, “Sorry, Bro,” a masterclass of anticlimax and narrative structure, resides in Season 4; and for that, it will ever have my gratitude.
2. Season 1
HIMYM took a few years to find its comic voice — especially for Barney — but not its storytelling voice, which was incisive and evocative from the start. Ted’s reckless, swooning approach to romance clashing with Robin’s measured, hesitant approach — both contrasting to Barney’s playboyism and Marshall and Lily’s settling down — generated some fantastic stories and genuine insights. It’s the dramatic, almost auteur-style, dimensions of early HIMYM that make this season so unique and rewatchable, even if the show’s funniest gags were a year or two away.
1. Season 2
Ironically (or, perhaps, instructively) HIMYM‘s best season came when it made no pretenses at striving towards its title. Ted simply dated Robin. With slightly less structural pretense than other seasons, the show focused on telling the best possible stories. The show was at its peak writing power, so almost every outing was a winner. It’s hard to go more than a few episodes without running into a classic. A few favorites: “Ted Mosby: Architect” for the great twist ending; “Lucky Penny” for telling its story in reverse order; “Arrividerci, Fiero” for giving us the funniest ‘flashback’ episode the show ever did; “Swarley” for, well, everything (especially Barney’s nickname and “crazy eyes”); and, of course, “Slap Bet,” HIMYM‘s general consensus best episode.