It’s hard to believe it’s been twenty years since The Office first premiered, bringing us into the world of Dunder Mifflin and changing TV comedy forever. The series gave us countless unforgettable moments — some hilarious, some heartwarming, and some so cringeworthy we had to pause just to recover. To honor two decades of The Office, let’s relive five of its most legendary moments.

View this post on Instagram

A post shared by Peacock (@peacock)

5. Michael and Holly’s Engagement (Season 7, Episode 18 – “Garage Sale”)

Michael Scott, the world's most awkward boss, had spent years searching for love, and with Holly Flax, he had finally found his perfect match. Their relationship, full of humor and vulnerability, became one of the most heartwarming storylines in The Office. So, when Michael decided to propose, he went all out – pouring his heart into a gesture that was as grand and genuine as his love for Holly.

He began by taking her on a walk through the office, pointing out the places where important moments in their relationship had unfolded. The journey led them to the kitchen, where their coworkers stood holding candles, creating a path for Holly to walk through. One by one, each employee, as part of Michael's elaborate plan, asked Holly to marry them, and she politely declined each time, not realizing that Michael was the one with the final proposal.

Finally, Michael led Holly to her desk. Now surrounded by dozens of candles. He dropped to one knee, his nerves getting the best of him as he fumbled through his speech. But before he could even ask the question, the fire sprinklers went off due to the flames from the candles, soaking the entire office. Despite the chaos, Michael continued, asking Holly to marry him with all the sincerity he could muster. And in that drenched, imperfect moment, Holly said yes.

As the office erupted in congratulations, Michael shared one last surprising twist — he and Holly were moving to Colorado. It was a bittersweet farewell, but it marked the beginning of a new chapter for Michael, who had finally found the love and happiness he had always longed for.

4. Jim and Pam’s Wedding (Season 6, Episodes 4 & 5 – “Niagara: Part 1 & 2”)

The love story of Jim and Pam is the heart of The Office, and their wedding was the ultimate payoff for fans who had been invested since season one. But in true Office fashion, things didn’t go smoothly. Their coworkers completely disregarded their one rule: don’t mention Pam’s pregnancy to her conservative grandmother. Kevin wore tissue boxes for shoes, Andy tore his scrotum, and Michael somehow ended up rooming with Pam’s mom.

But despite all the chaos, Jim and Pam had a secret plan. Before their big ceremony, they snuck away to get married on a boat at Niagara Falls — just the two of them. It was simple, it was perfect, and it was them. When they returned to the church, they let their friends and family have their chaotic moment, dancing down the aisle to Chris Brown’s "Forever" in a scene inspired by a real viral wedding video.

It was messy, ridiculous, and beautiful — just like their love story.

3. The Iconic Fire Drill (Season 5, Episode 13 – “Stress Relief: Part 1”)

Let's not forget about Dwight’s chaotic fire drill. Convinced his coworkers weren’t taking his fire safety lessons seriously, Dwight decided to stage an emergency — by actually setting a fire (kind of). He lit a trash can on fire, heated up door handles, barricaded exits, and even tossed a cat through the ceiling in a panic.

Chaos erupted. Angela screamed for her cat, Oscar climbed through the ceiling, Michael tried to break a window with a chair, and poor Stanley suffered a heart attack in the middle of it all.

As punishment, Michael was forced to hold a CPR training session, which led to another iconic moment: Dwight cutting the face off the CPR dummy like Hannibal Lecter. The entire sequence is a masterclass in absurd comedy, and it remains one of the most rewatched scenes in Office history.

2. The Infamous Teapot (Season 2, Episode 10 – “Christmas Party”)

Jim’s love for Pam was built on small moments, and no moment encapsulates that better than the teapot.

During the office’s Secret Santa exchange, Jim carefully chose a teapot for Pam, filling it with little mementos — inside jokes, memories, and a heartfelt note confessing his feelings. But when Michael turned the exchange into a chaotic Yankee Swap, Pam ended up trading the teapot away for an iPod.

After some maneuvering, Jim got the teapot back to her, but at the last second, he held back his note. He wasn’t ready. This scene perfectly captured what made The Office so special — it wasn’t just about the comedy, it was about the depth of these characters. Years later, in the final season, Pam finally got to read Jim’s note, bringing everything full circle.

1. The Best Prank Ever (Season 9, Episode 25 – “Finale”)

The series finale of The Office was a love letter to fans, and Dwight and Angela’s wedding was the perfect way to bring everything full circle. Their relationship had been a rollercoaster for years, but when Dwight finally realized Angela was the love of his life, he wasted no time in making her his wife.

In classic Schrute fashion, the wedding took place on his beet farm, with Angela arriving in a trunk (a tradition, according to Dwight). The ceremony was as bizarre as you’d expect, complete with Mose serving as a “kidnapper” and an uncomfortably long first kiss.

But what made this moment truly special was Jim’s final prank on Dwight. As best man, Jim informed him of a Dunder Mifflin tradition — choosing an “honorary best man.” And who did Jim pick? None other than Michael Scott.

Seeing Michael return for the wedding (“That’s what she said!”) was the emotional gut-punch fans didn’t know they needed. His presence was the ultimate nod to how much these characters had grown and how The Office would always be a family.

Honorable Mentions

Michael’s Goodbye (“Goodbye, Michael” – Season 7, Episode 22): A heartbreaking yet perfect sendoff for the world’s best boss.

Kevin’s Famous Chili (“Casual Friday” – Season 5, Episode 24): A tragedy in three acts.

Photo Credit: @theoffice on Instagram.