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The Best How I Met Your Mother Episodes, Ranked

How I Met Your Mother cast
(Image credit: CBS)

Kids, in the winter of 2022, Hulu debuted How I Met Your Father - which, as the title alone should suggest, is a gender-swapped update of How I Met Your Mother, which chronicled Ted Mosby’s (Josh Radnor) quest to find “The One” amid various misadventures with his friends in New York City. Narrated by the late Bob Saget (who was honored on the premiere of the new series) as Future Ted, the clever sitcom ran for nine seasons on CBS, amounting to a total of 208 episodes that made fans laugh, cry, and after the series finale even boil with rage (though Radnor didn't think fan response was that bad).

Upon the premiere of the spin-off, I could not help but be reminded of some of the most legen- wait for it…DARY moments from the original, which were still pretty fresh in my mind after a relatively recent full-scale binge, and having already seen the bulk of series more times than I can count. Thus, I had no problem accepting the challenge to compile my picks for the top 10 best episodes of How I Met Your Mother, starting with an early one that is still pretty awesome, okay?

Josh Radnor on How I Met Your Mother

(Image credit: CBS)

10. Okay, Awesome (Season 1, Episode 5) 

Robin (Cobie Smulders) gets her, Ted, and Barney (Neil Patrick Harris) into the prestigious club, Okay, while Marshall (Jason Segel) and Lily (Alyson Hannigan) host an insufferably boring wine tasting. Eventually, they all come together at the club, but the experience is less-than “okay” thanks to unnecessarily loud music, overpriced drinks, strict bouncers, broken teeth, and Barney’s awkward surprise reunion with his cousin.

“Okay, Awesome” is one of the funniest episodes of the show’s debut season, especially for its spot-on depiction of why, as Ted and Jayma Mays’ (one of many actors you may have forgotten were on the sitcom) coat check girl agree, “clubs suck.” The episode is also essential for getting to know the How I Met Your Mother cast of characters as it is one of the first to show them all in vulnerable and uncomfortable states at a place intended for letting loose.

Jason Segel

(Image credit: CBS)

9. Spoiler Alert (Season 3, Episode 8) 

Another episode that is a must for getting to know the HIMYM characters is a Season 3 classic that actually sees the gang get to know each other better. It starts when the others clue-in Ted to his new girlfriend’s excessive talking habit, something he never realized until then, setting off a chain reaction that exposes everyone’s previously unnoticed flaws.

“Spoiler Alert” is yet another prime example of HIMYM’s relatable humor, since rude awakenings to your family and friends’ irritating habits is something we all go through, unfortunately. Yet, as the episode also proves, those little things are easily overshadowed by what you love about them at the end of the day. 

Adam Paul as Mitch on How I Met Your Mother

(Image credit: CBS)

8. The Naked Man (Season 4, Episode 9) 

Season 4 saw Ted at his lowest after ex-fiancée Stella (Scrubs and Rick and Morty cast member Sarah Chalke) left him at the alter, but what helped him come out of his shell was a seduction technique that inventor Mitch (Adam Paul) calls the Naked Man. After the move works for Mitch on Robin, the rest of the gang put its guaranteed “two-out-of-three” success rate to the test.

There is not much to learn from this particularly raunchy episode - except, maybe, that trying the Naked Man in real life would most likely end the way it does for Barney. However, there is plenty of endearing humor amid its raunchiness, from the gang listing various reasons to have sex to Ted and Barney trading their own variations of the titular move over the phone.

Josh Radnor on How I Met Your Mother

(Image credit: CBS)

7. Right Place, Right Time (Season 4, Season 22) 

The damaging effects of Ted’s doomed engagement to Stella were a defining theme of Season 4 that came to a surprising peak in one of the series’ most inspiring episodes. Future Ted teaches his kids a lesson in fate by recalling a series of disparate circumstances that would ultimately guide him toward a life-changing moment: crossing paths with Stella and Tony (former Daily Show correspondent Jason Jones), who would later offer him a job teaching architecture.

A major theme of How I Met Your Mother as a whole is how the outcome of our lives are determined not just by our decisions, but by outsider circumstances that unexpectedly and mysteriously become instrumental in achieving our destinies. “Right Place, Right Time” brings that concept to the forefront in a clever, thought-provoking, and structurally inventive way.

Ashley Williams and Josh Radnor on How I Met Your Mother

(Image credit: CBS)

6. Drumroll, Please (Season 1, Episode 13) 

Speaking of chance meetings, Season 1 almost had us convinced that “The Mother” was Victoria (Ashley Williams), with whom Ted spends a romantic evening at Stu and Claudia’s wedding reception with no intention of meeting again until he becomes smitten with her. Little does he know, Robin holds the key to his reunion with this new love interest, but she is reluctant to reveal it having suddenly become smitten with him.

The grand love story that is our lives sometimes includes one brief, but perfect, encounter with another that doesn't need to last any longer. While Ted and Victoria do end up starting an ill-fated romance by the end of the episode, “Drumroll, Please” - referring to the lead-in before a kiss - is a wonderful meditation on those cherished moments.

Cobie Smulders on How I Met Your Mother

(Image credit: CBS)

5. Slap Bet (Season 2, Episode 9) 

Part of the fun of a relationship is learning new things about one another, such as the epic bombshell we learn about Robin in Season 2. Speculation over the root of her fear of malls leads the gang to discover her past as pop star Robin Sparkles, whose signature hit in Canada was “Let’s Go to the Mall.”

Few How I Met Your Mother episodes are as important to understanding the full narrative of the show as this one that introduces two recurring gags: Robin’s embarrassing career in show business and the titular “Slap Bet.” Barney slaps Marshall after incorrectly assuming his bet that Robin was a porn star was true and, as punishment, must endure five random slaps, which Marshall completes in Season 9.  

Neil Patrick Harris on How I Met Your Mother

(Image credit: CBS)

4. Game Night (Season 1, Episode 15) 

Speaking of epic bombshell discoveries, what we learn about Barney in Season 1 is arguably even more unbelievable. A simple game of “Marshgammon” turns into a night of groundbreaking reveals about one another, including Barney’s past as a meek, virginal hippie whose dreams of going to the Peace Corps with then-girlfriend, Shannon (Katie Walder), were crushed when she left him for a douchebag businessman.

Another valuable HIMYM lesson is how dramatically our personalities can change over time. “Game Night” spells this out in a dazzlingly funny way by tracing Barney’s evolution from an entirely different person to an Armani-clad commitmentphobe.

Neil Patrick Harris and John Lithgow on How I Met Your Mother

(Image credit: CBS)

3. Legendaddy (Season 6, Episode 19) 

Another life-changing moment for Barney was meeting his real father, whom he once believed was Bob Barker. In Season 6, he learns it is really his “Uncle Jerry” (John Lithgow) after he shows up at his doorstep and they spend an evening together that, according to Barney’s description, was “legendary.”

However, this story is a misdirect to hide that Jerry is really a “lame suburban dad” whom Barney claims he wants nothing to do with, which proves to be another misdirect. A lame suburban dad is all Barney ever really wanted and needed, as revealed in a climatic confrontation between the father and son that makes “Legendaddy” one of HIMYM’s most heartbreaking chapters.

Cristin Milioti on How I Met Your Mother

(Image credit: CBS)

2. How Your Mother Met Me (Season 9, Episode 16) 

Now, let’s talk about some real heartbreak, huh? We finally met “The Mother,” eventually revealed to be named Tracy McConnell (Palm Springs star Cristin Milioti), in the Season 8 finale and saw glimpses of her relationship with Ted throughout Season 9, but never really got to know her personally until Episode 200: “How Your Mother Met Me,” which follows the series’ full timeline from her perspective.

While on a journey to overcome the trauma of her boyfriend’s sudden death on her 21st birthday, Tracy helps Mitch discover the Naked Man’s two-out-of-three success rate, unofficially becomes acquainted with Ted in what he thought was his architecture course, and more classic callbacks. Putting a perfect cap on the already moving story is her tender ukulele rendition of “La Vie En Rose” on the night before Barney and Robin’s wedding, unaware that Ted can hear from the room next door.

Josh Radnor and a pineapple on How I Met Your Mother

(Image credit: CBS)

1. The Pineapple Incident (Season 1, Episode 10) 

In lieu of its many tender, inspiring, or thought-provoking moments that we have covered, I believe there is one episode above all others that best captures the essence of How I Met Your Mother as a story about choice and consequence, lessons learned, and the strange place life often takes us, all while being thoroughly hilarious. That episode is the Season 1 classic “The Pineapple Incident.”

The title refers to the fruit on Ted’s nightstand the morning he finds a woman in his bed, his ankle sprained, a strange phone number written on his arm, and no memory of what happened between his five shots of “Red Dragon” and the moment he woke up. In fact, the pineapple is the one thing left unexplained after the gang struggles to piece together Ted’s drunken misadventures with the clues they have, resulting in a suspenseful tale that, in typical HIMYM fashion, both celebrates debauchery and reminds you to proceed with caution.

And kids..., that's how we ranked the best episodes of How I Met Your Mother. Would you agree?

Jason Wiese
Jason Wiese

Jason has been writing since he was able to pick up a washable marker, with which he wrote his debut illustrated children's story, later transitioning to a short-lived comic book series and (very) amateur filmmaking before finally settling on pursuing a career in writing about movies in lieu of making them. Look for his name in just about any article related to Batman.