50. ''Nothing Good Happens After 2 a.m.''
Season 1, episode 18
They may have had a great season together, but Ted and Robin didn’t have the greatest start. Robin, realizing her feelings for Ted are real, calls him to come over one night. Future Ted regularly repeats the mantra ”Nothing good happens after 2 a.m.” but goes anyway. About to sleep together, the duo accidentally switch phones, and Robin discovers Ted lied to her when he said he ended things with Victoria. (Poor Victoria.) Not exactly a high point for Robin and Ted’s doomed love — but it left fans with good advice: After 2 a.m., just go to sleep. —Erin Strecker
49. ''The Goat''
Season 3, episode 17
The famed Bro Code was featured heavily in this episode about rules between friends. On the way to Ted’s 30th birthday party, Barney confessed to Ted he slept with Robin, and Ted counters that he doesn’t want to be friends anymore. As for the titular Goat? What a tease! Future Ted reveals that that actually went down at his 31st birthday party. —Erin Strecker
48. ''The Perfect Week''
Season 5, episode 14
Sure, the premise is kind of crass. But when Barney is close to scoring a ”perfect week” (seven women, seven days), the gang comes together at MacLaren’s to support him, before coming to the realization that they’ve all had kind of a bad week (scaring another couple away because you use the same toothbrush tends to do that, Lily and Marshall). Barney’s week of conquests isn’t exactly like sports, but it serves a similar purpose: Something silly to distract yourself with when life is hard. Bittersweet, yes, but also honest. —Erin Strecker
Season 2, episode 3
One of the things that made this show better than the average sitcom was the way it played with time and storytelling. This episode was like a play in three acts: ”The Marshall and Lily Part,” ”The Barney Part,” and ”The Me (Ted) and Robin Part.” The stories were both funny (Marshall’s calves!), and touching (Ted’s parents!) but the most exciting part was seeing how it all came together. —Erin Strecker
Season 4, episode 12
Robin and Ted are sleeping together! Robin and Ted are sleeping together! When Robin moves back into the apartment as Ted’s ”just friends” roommate, the two realize that in order to live together, it helps to also be hooking up. Which they do, for just a little while. They’re both fine with the new arrangement, until Ted realizes how much it’s hurting Barney and shuts it down. Robin is still oblivious, but this is one of the first times we see Ted step aside for Barney and Robin. —Erin Strecker
45. ''First Time in New York''
Season 2, episode 12
You never forget your first time, and fans will never forget hearing about the gang’s respective first times. Robin attempts to dissuade her little sister from having sex, and, in the process, in the lobby of the Empire State Building, Marshall, Lily, Barney and Ted attempt to support Robin by telling their own bad virginity tales, which gave fans a treasured Scooter memory as well as Barney pretending he was in Dirty Dancing. Bonus: At the end of the episode, Robin tells Ted she loves him. There’s a first time for everything. —Erin Strecker
44. ''The Playbook''
Season 5, episode 8
Any glimpse into Barney’s warped mind is a treasure, and in this episode, we get to see his Playbook — full of roles he can play to woo ladies — in action as he gets over his breakup with Robin. HIMYM is no stranger to list-style episodes, and this is one of its best: Barney playing out the Playbook with tactics like pretending to be a mopey Ted or a scuba diver are fun to watch and a welcome return to Old Barney after getting a taste of Relationship Barney. —Ariana Bacle
43. ''Single Stamina''
Season 2, episode 10
Say hello to Wayne Brady as James Stinson, Barney’s gay and equally legendary brother. The two love to play wingman for each other, but plot twist: Barney’s brother is engaged! Best quote is when James accuses Barney of being against gay marriage and Barney retorts, ”Not gay marriage. Marriage.” Look at you now, Barney! —Ariana Bacle
Season 2, episode 16
This episode could alternatively be titled ”Bad Decisions”: Lily volunteers to sit through Barney’s one-man show where she’s subjected to Barney saying the word ”moist” repeatedly and squirting her with a water gun; Robin gets rid of her dogs to make Ted happy; Ted ”throws away” everything from past girlfriends to please Robin but ends up putting it back in his apartment; Ted and Robin decide to live together after a blowout. But bad decisions make great TV, so no complaints here. —Ariana Bacle
41. ''Something New''
Season 8, episode 24
A lot happens in this emotional episode, including Ted telling Lily that he’s moving to Chicago because he still has feelings for Robin (tissue, please) and Marshall accepting a judgeship even though he has plans to move to Rome with Lily, but the biggest thing? This is where we finally get a look at the Mother, yellow umbrella in hand. She’s real, guys! —Ariana Bacle
40. ''Robots Versus Wrestlers''
Season 5, episode 22
Ted reaches the pinnacle of his over-the-top intellectuality in this episode when he takes everyone to a fancy party and starts reciting Dante’s Inferno in ”the original Italian” before having a satisfying-for-us moment where he realizes that yes, his friends were right, he is a douche. Meanwhile, Barney has a freak-out that the gang is falling apart, an especially emotional thought now that we’re nearing the series’ end and the gang actually may fall apart. —Ariana Bacle
39. ''Oh Honey''
Season 6, episode 15
Guest star Katy Perry does just fine as Zoey’s naive cousin, a hottie Future Ted remembers only as Honey. The real reason the episode works, though, is its nifty, twisty structure, a series of stories conveyed to an absent Marshall via flashbacks and phone calls. All of them lead up to Ted and Zoey’s first kiss, which was a big deal for literally dozens of Toey shippers. —Hillary Busis
38. ''The Duel''
Season 1, episode 8
An early half-hour that indicated HIMYM was very much on the right track: After learning that her little-visited apartment has been transformed into a Chinese restaurant, Lily officially moves in with Ted and Marshall. Things, uh, don’t go entirely smoothly, leading to the titular battle — an epic sword fight, which Ted and Marshall can’t help being psyched about even though they’re mad at each other. That’s a true bromance. —Hillary Busis
37. ''The Magician's Code (Part 1)''
Season 7, episode 23
Thirty minutes of milestones: Lily’s in labor! Lily’s giving birth! Lily and Marshall are naming their son Marvin Wait-for-it Eriksen! (Willing suspension of disbelief: Activated.) Elsewhere, Ted and Robin make amends, Marshall and Barney get an assist from a bus full of senior citizens, and season 7’s best supporting character — the ducky tie — gets plenty of screen time. —Hillary Busis
Season 4, episode 4
Behold, the birth of one of the show’s greatest running gags: the Intervention banner, unfurled first to get Marshall to stop wearing a dumb hat, then subsequently trotted out for everything from Barney’s magic tricks to Lily’s fake English accent. But there’s more than gags here; the episode also delves into the gang’s unease with their changing lives, as well as the reservations everyone but Ted seems to have about his engagement to Stella. (And we all know how that turned out.) —Hillary Busis
35. ''Band or DJ''
Season 8, episode 13
Real talk: The Ballad of Ted and Robin wasn’t always as engrossing as the show wanted it to be, particularly when HIMYM reached its twilight years. That said, this episode — which focused on Barney trying to win over Robin’s scary father as Ted tried to deal with his feelings about his pals’ impending nuptials — hit the right notes, both emotionally and mythologically. (See, if Robin and Barney had taken Ted’s advice and booked a DJ for the wedding, he never would have met a certain economics-loving bass player?.) Bonus: Lily and Ted’s mutual rooftop confessions took the show to a more honest place. —Hillary Busis
Season 7, episode 13
The death of Marshall’s dad was an emotionally exhausting arc that also brought out the best in the gang. But as evident in this episode — about Marshall’s attempt to continue his tailgating tradition by setting up camp at his father’s grave — it also made for some great solo Marshall moments. In this episode, he came to the realization that carrying on his father’s good-natured spirit was the most important tradition for him to embrace. Also in this episode, Barney and Ted finally lived out their dream of opening a bar named Puzzles, and that’s awesome. —Sandra Gonzalez
Season 3, episode 20
Ted proposed to Stella in this episode, but, if we’re being honest, it’s the movement on the Barney and Robin front that made this episode a standout. The moment we speak of was nothing huge — merely a look from hospitalized Barney to Robin, actually — but at this point, the RoBarn fire was still so new, that fans of the pairing took this as a sign of hope for these two. The legendary playboy was falling for a girl, one girl. That’s not just surprising, that’s a miracle. —Sandra Gonzalez
32. ''Tick Tick Tick...''
Season 7, episode 10
Ted and Marshall’s strange, ”sandwich”-caused adventure in this episode was worth the price of admission alone. But when you add to it the emotional weight of the Robin and Barney arc — at this point, she and Barney were dating other people but the episode ends with Barney hoping to woo Robin back with a romantic evening — it stands as an example of HIMYM‘s ability to balance the zany with the just-plain-heartbreaking. —Sandra Gonzalez
31. ''The Bracket''
Season 3, episode 14
After he’s randomly slapped by multiple women, Barney commandeers Ted and Marshall’s March Madness bracket to figure out which of his past conquests is sabotaging his love life. While he doesn’t solve the mystery in this episode (it turns out to be a certain head-shaving pop star), we are treated to a montage of his greatest pickup scams throughout the years. —Katie Atkinson
30. ''Trilogy Time''
Season 7, episode 20
The oft-mentioned Star Wars was a central part of this season 7 episode that revolved around Marshall and Ted’s vow to watch the trilogy every three years — lest the Dark Side win. Using each viewing as a mile-marker of sorts, Ted comes to realize he’s far from fulfilled his expectations for life — especially romantically. Watching Ted go through this difficult realization was a great and unexpected honest moment. Any feelings of sadness for Ted, however, melted away in an episode-ending flash forward to 2015, where we saw him sitting down for yet another Trilogy Time — this time, carrying his baby daughter. —Sandra Gonzalez
29. ''Atlantic City''
Season 2, episode 8
This is the time Marshall and Lily were married for 12 seconds. The couple decides to elope to Atlantic City, with friends in tow and without the judging eyes of Marshall’s family, but after Barney wins the money to pay for a wedding at sea, they decide they need to do it the right way. The boat-captain minister has already married them, however, so he has to ”undo” the wedding seconds later. —Katie Atkinson
28. ''Okay Awesome''
Season 1, episode 5
This one could be called ”How I Met Coat Check Girl.” Glee‘s Jayma Mays returned six seasons later as the only worthwhile woman Ted meets at a swanky hot spot with Robin and Barney. Meanwhile, Lily and Marshall escape their stuffy wine and cheese party to join the rest of the gang in da club, proving that growing up is overrated. —Katie Atkinson
27. ''The Pineapple Incident''
Season 1, episode 10
This episode exemplifies the show’s nonlinear storytelling, as we begin in Ted’s bed with a mystery girl and a pineapple and then unravel the previous night’s events. While the gang thinks it’s Robin between the sheets, it’s actually one-night stand (and future threesome possibility) Trudy. We never did find out what that pineapple was doing there…. —Katie Atkinson
26. ''Girls Versus Suits''
Season 5, episode 12
In the show’s 100th episode, we get the biggest Mother clues to date, as we learn that she is Cindy’s roommate and plays bass in a band — and we get a glimpse of her foot (we were taking anything we could get at that point). But the real star of this episode is the musical number at the end, as the whole gang suits up for ”Nothing Suits Me Like a Suit.” —Katie Atkinson
Season 5, episode 24
Combine the joy of seeing the gangs’ doppelganger’s with the emotional question of whether Lily and Marshall are ready for a baby, and you’ve got a great episode (not to mention season finale) of television from our favorite group of friends. Plus: Barney in elaborate costumes — how can you not love that? —Erin Strecker
24. ''Right Place Right Time''
Season 4, episode 22
HIMYM often grappled with big questions about destiny and fate (it’s one of Ted’s favorite topics, after all). This episode was all about how one choice (ideally completed with a yellow umbrella) can change your life. Meanwhile, Barney completed his 200th conquest (ugh?) and realized he might want something more when it comes to relationships. Cue meaningful look to Robin. —Erin Strecker
23. ''No Tomorrow''
Season 3, episode 12
St. Patrick’s Day finds Lily and Marshall staying at home (in their brand-new, crooked apartment!) while Ted joins Barney on the town. But while fans were used to Barney’s player ways, it’s a bit shocking to see Ted embrace his inner douche. Luckily, a wake-up chat with Marshall puts Ted back on track, and the night isn’t a total wash — Ted snags a yellow umbrella from the club and just misses the Mother. —Erin Strecker
22. ''Naked Man''
Season 4, episode 9
Yes, the premise is slightly creepy. But fans forgot about that while they were laughing at one of the best one-offs the show has ever created. Round of applause for the gang’s unsung superhero — you know it works two out of three times. —Erin Strecker
21. ''Something Blue''
Season 2, episode 22
The second part of Lily and Marshall’s wedding episode tackles the reception. But the real story involves a flashback that explains why Ted and Robin broke up. It was a long time in the making, but the deft execution allowed us to empathize with both characters?and, with Barney, cheer their next step. Excuse us, we’ve got something in our eye. —Erin Strecker
20. ''The Ten Sessions''
Season 3, episode 13
Ted repeatedly asked out his dermatologist, Stella, and she repeatedly refused. The episode is pretty standard — save for a guest appearance by Britney Spears(!) — but it’s the final moments that make it really something special: A one-shot, two-minute date that Ted planned for his short-on-time single mother lady love. Viewers swooned right along with her. —Erin Strecker
Season 3, episode 9
The third slap of the bet! The gang’s very own holiday is on display when Marshall creates a countdown website for Barney’s next slap. Fans also learn that Robin and Ted are having trouble being friends. Get used to it, guys. You’re going to be dealing with this for the next six seasons. Bonus: General Knowledge (*salute*) —Erin Strecker
18. ''Sandcastles in the Sand''
Season 3, episode 16
Robin Sparkles returns! But instead of just being a silly installment, guest star James Van Der Beek was a catalyst for Robin to wonder if she’s secretly her teenage self — who can’t relate to that? A standout episode for Cobie Smulders, it also introduced ”revertigo” and ended with Robin and Barney hooking up for the first time. All that and we got another Robin Sparkles music video (and it did not disappoint)! —Erin Strecker
17. ''Three Days of Snow''
Season 4, episode 13
”Snow” stands as one of the series’ most effective uses of time-twisting. After a massive snowstorm hit New York City, we followed the individual arcs of our characters over three days and not until the end did we realize that we were watching different points in time. Moreover, Marshall’s arranging of a marching band airport arrival for his wife capped off this clever half-hour with what would be one of the sweetest Marshall and Lily moments ever. —Sandra Gonzalez
16. ''The Final Page (Part 2)''
Season 8, episode 12
For weeks, the HIMYM writers baffled us by hooking up Barney with Robin’s coworker/frenemy Patrice. But it was all part of an elaborate plan for Barney to propose to the real love of his life, Robin, thus ending the era of playboy Barney once and for all. As a bonus, Ted gives his implicit blessing by delivering Robin to the site of the proposal — though we all know that book is never quite closed. —Katie Atkinson
15. ''Spoiler Alert''
Season 3, episode 8
True friends overlook (or tolerate) one another’s most annoying qualities, but when the gang decides Ted’s new girlfriend Cathy talks too much, they let the cat out of the bag about everyone else’s flaws. Spoiler alert! Robin doesn’t know how to use the word ”literally,” Ted corrects everyone, Lily chews too loudly, and Barney speaks in falsetto. Also, this is where Marshall (who turns everything into a song) finds out he passed the bar exam. —Katie Atkinson
14. ''Arrivederci, Fiero''
Season 2, episode 17
In this love letter to Marshall’s beloved Pontiac Fiero, the gang shares their favorite memories of the car as it breaks down just shy of the 200,000-mile mark. With the Proclaimers’ ”I’m Gonna Be (500 Miles)” on loop, this episode lovingly reflects on the group’s past as they try to push the dying ride over the finish line. —Katie Atkinson
13. ''Come On''
Season 1, episode 22
The season 1 finale really tests the sitcom limits, offering up the romantic high of Ted winning Robin back and the emotional low of Marshall losing Lily. Before the 200th episode, show creator Craig Thomas told EW this was his favorite of the series: ”To me, that’s like the essence of the show and why the show works, because it’s life all happening at once. It’s joy and it’s sadness and it’s reality.” —Katie Atkinson
12. ''Game Night''
Season 1, episode 15
A rousing game of ”Marshgammon” prompts each of the friends to admit their most embarrassing story — and the most revealing tale belongs to Barney, as we learn how a Peace Corps-bound hippie became the suited-up lady killer we know and love. This is also where Victoria learns of Ted’s romantic past with Robin, setting up a rift that would never truly go away. —Katie Atkinson
11. ''The Symphony of Illumination''
Season 7, episode 12
”Illumination” begins with Robin, instead of Ted, talking to her future kids. But over the course of the half-hour, we learn that Robin and Barney aren’t actually expecting a baby — because Robin can’t have a baby. And those ”future kids” she’s talking to? They don’t exist, because she never becomes a mom. This twist is on par with the surprise death of Marshall’s dad for the saddest ending in HIMYM history. —Katie Atkinson