The Office turns 20: Revisit 12 of the hit comedy’s all-time greatest episodes

It’s hard to believe, but The Office — that is, the US version that transformed the mundane world of paper sales into an all-time comedy masterpiece — celebrates its 20th anniversary this coming week. That’s right, the very first episode aired on NBC this month back in 2005, introducing us to Michael Scott, Jim and Pam, Dwight Schrute, and the rest of the Dunder Mifflin crew.

From its humble beginnings as a remake of the British series, The Office quickly found its own unique voice, blending cringe comedy with heartfelt storytelling and giving us one of the most beloved sitcoms in the history of TV. And as Brian Baumgartner (a.k.a. Kevin Malone) told me back in 2020, for a piece I wrote about Brian’s then-new Office podcast, the cast of the show felt they were onto something special almost immediately:

“I will say, from the second episode we shot, Diversity Day, I remember specifically being very aware that what the show was doing was special and unique … I specifically remember as we were shooting day after day, almost exclusively in the conference room, that if people gave the show a shot, we had the chance to be doing something special. You know, that episode (Diversity Day) focused on race. And what we were doing, what we were talking about, and the way we were talking about real issues, hopefully in a funny way, was something that really hadn’t been done since All In The Family.”

Fast forward to 2025, and the legacy of The Office is still going strong. In fact, a new iteration of the show is coming to Peacock later this year. The setting will shift to the office of a dying newspaper, with at least one familiar face (Dunder Mifflin accountant Oscar Martinez) set to appear.

But before we dive into the next chapter of The Office, let’s take a trip down memory lane. In honor of the show’s 20th anniversary, here are 12 of the best episodes ever, episodes that I’ve always thought best capture the magic, hilarity, and heart that made The Office such a phenomenon.

The most unforgettable Office episodes

The Dundies. The annual Dundie Awards at Chili’s brought us classic Office humor at its finest. Pam gets drunk, Michael tries (and fails) to be a beloved host, and we get the first glimpse of just how great Jim and Pam can be together. “Was this year’s Dundies a success?” Michael cluelessly reminisces at the end. “Well, let me see. I made Pam laugh so hard that she fell out of her chair and she almost broke her neck. So I killed. Almost.”

Office Olympics. Jim and Pam organize an office-wide Olympics while Michael unknowingly signs his life away on a condo. The sight of Michael getting emotional over his homemade “gold medal” is peak Office charm.

Casino Night. The Season 2 finale is a perfect mix of comedy and heart, featuring the long-awaited, tear-inducing moment when Jim confesses his feelings for Pam. Oh, and let’s not forget Michael’s two dates. “It’s also the only time Kevin wears glasses,” one Redditor notes. “So he clearly NEEDS glasses yet never once wears them for his job… as an accountant.”

The Injury. Michael burns his foot on a George Foreman grill and expects the office to treat him like a war hero. Instead, Dwight concusses himself while trying to help (giving us one of my favorite off-the-cuff Dwight moments — when the hospital asks him for his middle name, and Dwight answers: “Danger”). A masterpiece of physical comedy and oblivious Michael Scott behavior.

Business School. Ryan invites Michael to speak at his business class, and the result is a motivational speech for the ages. “A good manager doesn’t fire people,” Michael later tells Ryan. “He hires people and inspires people. People, Ryan. And people will never go out of business.” Meanwhile, Dwight chases a rogue bat through the office, and Pam’s art show gives us one of the sweetest Michael-and-Pam moments ever.

Beach Games. Michael treats a beach day as a bizarre Hunger Games-style competition to find his successor, while Pam finally finds her voice in a powerful, emotional moment that sets the stage for her and Jim’s future.

The Job. Jim and Karen head to New York to interview for a corporate job, but the real emotional payoff comes when Jim surprises Pam back in Scranton, bringing us one of the most heartwarming moments in the show’s history. “It’s a date!”

Fun Run. Michael hits Meredith with his car, and in an attempt to “make things right,” he organizes the most disorganized charity 5K ever, complete with carb-loading fettuccine Alfredo and Dwight mercy-killing Angela’s cat, Sprinklers.

The Deposition. Michael’s deposition in Jan’s wrongful termination case is equal parts cringeworthy and brilliant. From his inability to grasp legal strategy to his betrayal by Toby, this episode is peak awkward Office.

The Dinner Party. The most painfully hilarious episode of The Office ever? Possibly. Michael and Jan invite Jim, Pam, Andy, and Angela to their condo for a dinner party that quickly spirals into absolute chaos — complete with a plasma TV the size of a laptop and loads of uncomfortable relationship drama.

Stress Relief. This two-part episode opens with the single greatest cold open in TV history: Dwight’s fire drill-gone-wrong, which sends Stanley into cardiac arrest (“No, no, no! You will not die, Stanley! Barack is president Stanley! … I’m gonna give him mouth to mouth.”). Throw in Michael’s bizarre CPR training session (hello, Stayin’ Alive), and you’ve got an all-time classic.

Niagara: Parts 1 and 2. Jim and Pam’s wedding was always going to be emotional, but the unexpected dance sequence, the boat ceremony, and Kevin’s tissue-box shoes make this one of the most joyous and hilarious Office episodes ever. It reminds us that even in the most special of moments, life is messy, unpredictable, and full of surprises.

The NBC classic still reigns supreme

Two decades later, The Office remains as hilarious and quotable as ever. Whether you’ve watched it once or a dozen times (let’s be real, it’s more like a dozen), these episodes remind us why we fell in love with Dunder Mifflin in the first place. And with a new Office on the way, the legacy is still growing.

So, which of these episodes are you rewatching first? Or did your favorite not make the list? Either way, let’s raise our Dundie trophies and toast to 20 years of one of the greatest sitcoms of all time.