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The 25 Best Moments From ‘The Office’

From the Dundies to the dinner-party house tour to Jim and Pam’s first kiss, a totally subjective and absolutely definitive ranking of the show’s most hilarious and heartfelt highlights

Photo illustration of The Office

PHOTO ILLUSTRATION BY MATTHEW COOLEY. NBCU PHOTOBANK, 6; COLLEEN HAYES/NBCU PHOTOBANK, 2; JUSTIN LUBIN/NBCU PHOTO BANK; DANNY FELD/NBCU PHOTOBANK; TYLER GOLDEN/NBC/NBCU PHOTO BANK

Twenty years ago this week, The Office premiered on NBC. The network was in a mild state of panic at the time. Friends and Frasier had both recently ended, Matt LeBlanc’s Friends spinoff Joey was flailing in the ratings and costing them a fortune, and ER was long past its prime. While the original U.K. version of The Office, an acerbic cringe comedy starring Ricky Gervais, had been a cult favorite, few people thought a U.S. adaptation — centered on the mundane lives of employees at a struggling paper company in Scranton, Pennsylvania — would do much to turn around the network’s fortunes, especially since the most famous face on the show was a former Daily Show correspondent.

The show was nearly cancelled after a mere six episodes, but ratings slowly started to climb in the second season. Steve Carell and the writers found ways to make Dunder Mifflin regional manager Michael Scott lovable despite his annoying quirks. Everyone became obsessed with Jim and Pam’s will-they-won’t-they dynamic, and Rainn Wilson uncovered the heart buried inside Dwight Schrute, a beet farmer/paper salesman/wannabe authoritarian he was born to play.

The Office picked up enough momentum that it inspired NBC to give other quirky shows like 30 Rock, Parks and Recreation, and Community a shot, then became exponentially more popular years after it went off the air thanks to its arrival on Netflix. It’s not even remotely hyperbolic to call it the most beloved sitcom of the past quarter century.

In honor of its milestone anniversary, we prepared a list of the show’s 25 greatest moments. Like The Office itself, some of them are very silly, others are quite poignant, and several are a beautiful combination. (For much more on all this, check out my book The Office: The Untold Story of the Greatest Sitcom of the 2000s: An Oral History.)

From Rolling Stone US

2

Jim Kisses Pam

There’s a lot happening in the first two seasons of The Office, but the central storyline is Jim’s desperate crush on Pam. She clearly has feelings for him, too, but can’t act on them because she’s engaged to Roy, a warehouse worker who’s painfully wrong for her. At the end of the Season Two finale, Jim gathers up the nerve to tell Pam how he feels when they’re alone in the parking lot following a night of casino games in the warehouse. “I was just… I’m in love with you,” he says. “I’m really sorry if that’s weird for you to hear, but I needed you to hear it. Probably not good timing, I know that…I just needed you to know, once.” She doesn’t know how to respond or even feel, but tells him she’s sorry if he “misinterpreted things.” He walks away with tears in his eyes, but reemerges in the office when she’s calling her mother and kisses her, wrapping up one of the greatest seasons in television history.Best Line: “I don’t know, Mom. He’s my best friend.”

1

Kevin Spills the Chili

It was extremely hard (that’s what she said) to pick the singular greatest moment in the history of The Office. We weighed various Jim and Pam moments, key scenes where Michael Scott showed real growth, or even the best Jim and Dwight pranks. But in the end, we went with Kevin spilling chili all over the floor. The cold open lasts a mere 36 seconds, has nothing to do with the episode, and Kevin Malone (Brian Baumgartner) is the only character we see. But the contrast between the audio of him explaining how he cooks his delicious chili and footage of him spilling it on the floor and caking it all over himself as he pathetically tries to scoop it back in never stops being funny. It would have been funny in a silent movie from 1902. It’ll be funny 500 years from now. And Brian Baumgartner executes the scene flawlessly. It’s such a beloved moment that he wrote his own chili cookbook a few years back. (Office trivia: Aaron Shure wrote the scene, which was originally a bit longer and included a moment where Jim and Andy show up and wonder why the office smells like chili. Read the original draft here.)Best Line: “The trick is to undercook the onions. Everybody is going to get to know each other in the pot.”