It’s been 20 years since The Office first clocked in, and while the show gave us endless awkward silences, iconic pranks, and the world’s greatest boss (self-proclaimed), it also delivered some hilariously unforgettable musical moments. From cringeworthy performances to surprisingly touching songs, here are ten of the best musical moments in The Office.
1. Andy’s Banjo Serenade for Angela
When Andy Bernard sets his sights on wooing Angela, he does what any self-respecting Cornell a cappella alum would do—serenades her with a banjo. His rendition of “Take a Chance on Me” (complete with backup vocals via Bluetooth) is both over-the-top and completely endearing. Too bad Angela was more into her secret rendezvous with Dwight than Andy’s musical talents.
2. Michael and Dwight’s “My Humps” Performance
If you’ve ever wanted to hear Steve Carell and Rainn Wilson duet on a Black Eyed Peas song, The Office delivered. Watching Michael and Dwight passionately perform “My Humps” in the Dunder Mifflin parking lot (complete with dance moves) is a moment of pure chaotic energy that perfectly sums up their friendship.
3. Kevin’s Band, Scrantonicity
Kevin Malone doesn’t say much, but when he does, it’s usually about his Police cover band, Scrantonicity. Their big moment comes when they play at Phyllis’ wedding—against Kevin’s better judgment, since he’d rather be performing at Pam and Roy’s nuptials. Watching Kevin absolutely own “Roxanne” is a reminder that, beneath his quiet exterior, Kevin was a true rock star at heart.
4. Michael’s “Goodbye Toby” Song
Michael Scott’s rivalry with HR rep Toby Flenderson is the stuff of legend, so when Toby finally leaves Dunder Mifflin, Michael celebrates in style. His original song, “Goodbye Toby,” set to the tune of Supertramp’s “Goodbye Stranger,” is equal parts giddy and unhinged. Bonus points for Holly thinking it’s a beautiful, heartfelt moment instead of the ultimate insult.
5. The Dundies’ “You Had a Bad Day”
Every Dundies ceremony is an experience, but nothing tops Michael Scott’s dramatic, off-key rendition of Daniel Powter’s “Bad Day” after getting banned from Chili’s. His emotional performance, complete with a sad, slow dance, is both hilarious and oddly relatable—because who hasn’t felt personally victimized by a karaoke mic at least once?
6. Andy and Dwight’s Duel with “Take Me Home, Country Roads”
Andy and Dwight don’t always see eye to eye—especially when it comes to Angela. But for one brief, magical moment, their shared love of music unites them in a soulful duet of John Denver’s Take Me Home, Country Roads on the office stairwell. The moment is unexpectedly heartwarming… until they remember they hate each other and get back to fighting.
7. Darryl’s “Ain’t No Party Like a Scranton Party”
Darryl Philbin was The Office’s secret musical genius, and nowhere is that clearer than in his original banger, “Ain’t No Party Like a Scranton Party.” With an assist from Michael, this workplace anthem is so catchy that even corporate bigwig Jo Bennett gets in on the fun. Darryl deserved a Grammy. Or at least a Dundie.
8. Pam and Jim’s Wedding Dance
The Office’s take on the viral “Forever” wedding entrance dance was pure chaos, featuring Kevin in Kleenex box shoes, Michael getting way too into it, and Jim and Pam watching in amused horror. It was both a perfect parody and a heartfelt tribute to their offbeat but lovable work family.
9. Andy’s “I Will Remember You” Breakdown
After failing spectacularly as regional manager, Andy bids farewell to Dunder Mifflin with an emotional (and, of course, pitch-perfect) a cappella performance of I Will Remember You. It’s hilarious, it’s cringe, it’s peak Andy Bernard. Even Erin looks confused about whether she should laugh or cry.
10. The Entire “Threat Level Midnight” Musical Number
Michael Scott’s passion project, Threat Level Midnight, was a masterpiece in every way—but the highlight was undoubtedly the absurdly catchy dance number, “The Scarn.” Featuring Michael doing the world’s worst dance moves while a reluctant office staff sings along, it’s a moment of pure comedic gold that proves Michael was, if nothing else, committed to his art.
11. The “Nobody But Me” Office Dance Party
When Michael leaves Dunder Mifflin, the office throws an impromptu farewell dance party to The Human Beinz’s Nobody But Me. What starts as a simple moment of celebration turns into pure chaos, with characters like Andy, Erin, and even stoic Stanley breaking out their best (and worst) dance moves. It’s a scene that perfectly captures The Office’s ability to mix heartfelt goodbyes with ridiculous humor.
From banjo ballads to unforgettable parodies, The Office knew how to mix music and comedy like no other.
