Premiering in 2005, How I Met Your Mother took over from Friends as the go-to sitcom about young New Yorkers navigating through life and love in the city. Hopeless romantic Ted (Josh Radnor) is looking for his soulmate, and the series is framed as a seemingly endless story that an older Ted is telling his kids about how he met their mom. But the show is more about the journey than the destination, and there are plenty of detours along the way. While we don’t learn who the Mother (Cristin Milioti) is until the final season, we get to watch the many entertaining escapades of Ted and his friends over the course of nine years.
Despite its polarizing finale, How I Met Your Mother made us laugh for almost a decade and cemented its place in the cultural lexicon. These are the episodes that we think are the most memorable of the series.
The Pineapple Incident (Season 1, Episode 10)
This show likes to play with time, which lends itself well to a Rashomon-style episode about characters trying to piece together a night of drunken shenanigans. After taking 5 “Red Dragon” shots, Ted wakes up with a woman in his bed, a pineapple on his nightstand, and no memory of the night before. He also discovers that he has a sprained ankle and his coat is burnt.
Ted asks his friends what happened and finds out his wild night included falling off a table while singing karaoke, being set on fire by Barney (Neil Patrick Harris), and drunk dialing Robin (Cobie Smulders) multiple times. From the information he gathers, he thinks the woman in his bed is Robin, but it’s actually a girl named Trudy who he met at the bar. Ted took the shots to stop overthinking, but it ended up making things more complicated.
The source of the mysterious pineapple wasn’t revealed until after the series ended. A deleted scene from a season 9 episode shows Ted finally remembering how he stole the fruit from The Captain’s doorstep.
Come On (Season 1, Episode 22)
Not one to give up easily, Ted tries to win over Robin, but she’s hesitant to start a relationship with him. Ted is also dismayed to learn that she's going on a camping trip with a co-worker who wants to date her. He attempts to do a rain dance, hoping that a storm would cause the trip to get cancelled. Even though this is a dumb idea, it actually does rain and Robin decides she wants to be with Ted.
While Ted finally gets the girl, Marshall (Jason Segel) loses the love of his life. Lily (Alyson Hannigan) gets accepted for an art fellowship in San Francisco and she wants to do it, even though their wedding is coming up. Marshall is afraid that if she leaves, she’ll change her mind about marrying him. They have a big fight that results in Lily giving her ring back. The first season ends with an elated Ted finding a dejected Marshall sitting in the rain.
Swarley (Season 2, Episode 7)
This episode gets its title from Barney’s misspelled name on a coffee cup. This random little thing becomes a joke throughout the episode, as the gang continually refers to Barney as Swarley and he gets more and more upset. Still single after breaking up with Lily, Marshall asks out the barista who wrote Barney’s name wrong. Ted and Barney warn him that this girl has “crazy eyes,” which is a bad sign. Lily and Marshall are a great couple, so it’s weird to see him dating someone else. Lily obviously has a problem with it too, as she interrupts his date to stop him from kissing another woman.
She runs away embarrassed, but Marshall follows her and tells her she has “crazier eyes than anybody that I have ever met.” Clearly missing each other, they kiss. It’s a relief to see them finally back together, and thankfully, they remain a stable couple for the rest of the show.
Slap Bet (Season 2, Episode 9)
This classic episode introduces two running jokes that continue for the rest of the series: Robin’s pop star alter ego Robin Sparkles, and the slap bet between Marshall and Barney. Robin hates malls and won’t explain why, leading the gang to wonder what her secret is. Marshall thinks that Robin got married at a mall, while Barney guesses that she’s done porn. They make a bet that whoever is right gets to slap the other.
The truth eventually comes out when Barney uncovers a video from Robin’s past. Automatically assuming it's porn, he slaps Marshall. It’s actually the gloriously cheesy music video for the song “Let’s Go to the Mall,” from Robin’s days as a teen pop star in Canada. The amazing parody of 80s music videos (because “the 80s didn’t come to Canada til like ’93”) features Robin dancing in a jean jacket and flying with a robot. This unexpected and hilarious reveal means that Barney was wrong, and Marshall gets to slap him five times whenever he wants. He doles out the first slap right away, and saves the others for future episodes.
Something Borrowed (Season 2, Episode 21)
It’s Marshall and Lily’s wedding day and everything is going wrong. Lily’s ex-boyfriend shows up in an effort to win her back, a groomsman tackles the photographer, and the harp player is in labor. To make matters worse, Marshall unwittingly gets frosted tips in his hair and shaves his head in a moment of panic.
With the bride and groom in distress, the gang meets up outside and Ted suggests that the couple get married twice. They can have the small outdoor wedding they had initially wanted before going through with the big disastrous ceremony. Barney, who got ordained for the occasion, officiates while holding back tears. Lily and Marshall exchange adorable vows that list the reasons they love each other. The simple, intimate wedding is much more fitting for the couple. A great sitcom wedding should be both funny and sweet, and this episode perfectly pulls it off.
Slapsgiving (Season 3, Episode 9)
In this festive episode, Lily and Marshall are hosting their first Thanksgiving. Lily is preparing dinner, but Marshall is getting ready to deliver the third slap of his slap bet with Barney. He mercilessly taunts Barney and even creates a website with a timer counting down to the moment of the slap.
Meanwhile, Ted and Robin are still dealing with the aftermath of their breakup. They hang out together with the rest of the group, but feel awkward when it’s just the two of them. They decide they shouldn’t be friends anymore, but an inside joke between them resurfaces during dinner and they realize that maybe there is hope for their friendship.
Even though Lily put a stop to the slap countdown because it was ruining dinner, she lets Marshall slap Barney at the last second. With Barney reeling in pain, the gang gathers around the piano while Marshall plays a song he wrote for the event, titled “You Just Got Slapped.” Best Slapsgiving ever.
Ten Sessions (Season 3, Episode 13)
At an appointment to get his butterfly tramp stamp removed, Ted clicks with his dermatologist Stella (Sarah Chalke). She’s not allowed to date patients, so Ted says he’ll ask her out after the ten sessions it takes to get rid of the tattoo. Stella warns him that she’ll say no, but he keeps trying to impress her. During this time, her receptionist Abby (Britney Spears) develops a crush on Ted, but he’s completely oblivious to this.
Marshall makes an appointment with Stella and finds out that she does like Ted. But when Ted asks her out after the last session, she still declines. He learns that she doesn’t have time to date because she has a daughter. He surprises her by taking her on a two-minute date during her lunch break, a very quick dinner and a movie. Ted’s romantic gestures can go overboard, but this one is actually really cute.
Three Days of Snow (Season 4, Episode 13)
A giant snowstorm hits NYC, delaying Lily’s flight back from Seattle. She and Marshall are considering letting go of their cute little traditions like calling each other at lunchtime, kissing on New Year’s Eve, and meeting each other at the airport. Even though Marshall wasn’t planning on picking Lily up from the airport this time, he decides to go anyway.
At MacLaren’s, the bartender leaves Ted and Barney in charge of the empty bar while they wait for their dates. However, their dates are members of a marching band, and they bring the whole band along with them. The guys seize the chance to fulfill their Cocktail-inspired dreams of running a bar, which they rename Puzzles (“People will be like, ‘Why is it called Puzzles?’ That’s the puzzle!”). When the bartender returns, they move the party back to their apartment.
The thankful band members help Marshall surprise Lily at the airport by playing “Auld Lang Syne.” It’s a very romantic moment that shows that some traditions should always be kept.
The Playbook (Season 5, Episode 8)
Loveable cad Barney Stinson became a fan favorite from the start with his ridiculous catchphrases and womanizing antics. Barney will go to great lengths to pick up women, so it’s no surprise that he has a book full of these outlandish schemes. The concept of the playbook is disgusting, but given that the plays have names like “The Lorenzo von Matterhorn,” it’s also pretty hilarious.
After ending a committed relationship with Robin, Barney is ready to play the field again and breaks out the playbook once more. We get to see his plays in action as he explains them to his friends, ending each scenario with a wink to the viewers. As he sits in the bar in a scuba suit getting ready to carry out a play called “The Scuba Diver,” Lily warns the girl he is targeting. Surprisingly, Barney admits that he’s taking his breakup with Robin pretty hard, causing the girl to feel sorry for him and give him a chance. It turns out this moment of vulnerability was just another scam and part of a larger play. You have to give it to Barney, he does think these things through.
Girls Versus Suits (Season 5, Episode 12)
The show’s 100th episode celebrates the milestone by giving us more clues about the Mother than ever before. Ted starts dating Cindy (Rachel Bilson), who won’t stop complaining about her roommate. This roommate is actually the mother, and Ted learns that his future wife plays bass guitar and creates paintings of robots playing sports. Ted discovers he has a lot in common with this mystery woman, but only gets a glimpse of her foot. He also accidentally leaves his yellow umbrella at her apartment, which plays an important role in their eventual meeting.
Meanwhile, Barney is facing a difficult choice. He has his eye on the new hot bartender at MacLaren’s, but she despises men who wear suits. She gives him an ultimatum: her or his suits. Barney launches into a giant musical number about how he would never give up his precious suits for a woman. But despite claiming “nothing suits me like a suit,” he changes his mind and hooks up with her anyway.
Last Words (Season 6, Episode 14)
The show does a great job of balancing humor with more poignant moments. One of the most emotionally resonant episodes takes place at the funeral for Marshall’s father, after he passed away suddenly in the previous episode. The gang accompanies Marshall to Minnesota for the service, but they aren’t sure how to cheer him up.
Marshall learns that the theme of the funeral will be his father’s last words to his family, and he’s upset that their last conversation wasn’t significant. He then realizes that he has a voicemail from his father on his phone, but he’s hesitant to listen to it. When he does decide to listen, he is disappointed to hear that it’s a pocket dial, and gives an impassioned speech to his friends about how unfair it is that his dad is gone. But at the end of the message, his father starts speaking and tells Marshall he loves him, giving him a little bit of comfort. Seeing Marshall’s loss makes the rest of the group reflect on their own relationships with their dads. This is a very sad episode for a sitcom, but it includes some powerful acting and important character development.
How Your Mother Met Me (Season 9, Episode 16)
In the show’s ninth season, we are finally introduced to the Mother, whose real name is Tracy. She turns out to be extremely likeable and charming, living up to the high expectations set for the character. The 200th episode of the series shines a light on her side of the story, revisiting scenes from past episodes to show her near misses with Ted throughout the years.
Unlike Ted, who has been searching for The One this whole time, Tracy had found her soulmate but he passed away tragically. After years of not dating, she starts seeing someone but is still not over her deceased love. Her boyfriend proposes to her while she’s in Farhampton to play in the band at Barney and Robin’s wedding. She turns him down and decides to move on from her past heartbreak. Alone at the Farhampton Inn, she sings a beautiful version of “Le Vie En Rose,” (showing off Milioti’s amazing voice) which Ted overhears. This episode helps the audience get to know and care about Tracy as a character after nine years of buildup.
Honorable Mentions
Game Night (Season 1, Episode 15): We learn about Barney's past life as a hippie, and how he became a suit-wearing lothario.
Arrivederci, Fiero (Season 2, Episode 17): The gang reminisces about their adventures in Marshall's old Pontiac Fiero. We can't hear "I'm Gonna Be (500 Miles)" without thinking of this episode.
Intervention (Season 4, Episode 4): The gang holds so many interventions for each other about silly things that they need an intervention for their interventions.
What's your favorite How I Met Your Mother episode? Let us know in the comments.