An enormous part of the success of Brooklyn Nine-Nine, the FOX-then-NBC sitcom about the escapades of a tight-knit group of detectives in a Brooklyn precinct, was André Braugher’s Captain Raymond Holt. Famous for Homicide: Life on the Street, another police procedural with a distinctly heavier vibe, Braugher brought all the gravitas of that role into the buffoonery of the Nine-Nine, providing both a counterweight to the squad’s frivolity and his own distinct brand of hilarity. With the heartbreaking confirmation of Braugher's recent passing, and in celebration of the power and humor Captain Holt brought to the series, we rank his funniest and most unexpected cold opens from his time on the opposite side of the law in Brooklyn Nine-Nine.

Brooklyn Nine-Nine

TV-14

Comedy

Crime

Comedy series following the exploits of Det. Jake Peralta and his diverse, lovable colleagues as they police the NYPD's 99th Precinct.

Release Date

September 17, 2013

Cast

Andy Samberg , Terry Crews , Andre Braugher , Stephanie Beatriz

Main Genre

Comedy

Seasons

8

Creator

Dan Goor, Michael Schur

9 Jake Calls Holt “Dad” – “The Apartment”

(Season 1, Episode 18)

After Detective Jake Peralta (Andy Samberg) tosses off an unthinking, “Thanks, Dad,” in response to some mild praise from Holt, the squad begins to roast him for it over his increasingly panicked denials. For most of the cold open, Holt has little to do other than attempt to defuse the situation. His authoritative presence is a solid and calming counterpoint to Jake’s spiral — only to culminate in Holt’s perfectly deployed “I believe you… son.” With just the barest hint of a smile, he offers Jake a game of catch. It’s the perfect capper to the joke and a crystal-clear combination of Holt’s dry-as-toast humor and his abiding love of messing with Jake — both traits that will reappear on this list.

8 Holt Has No Pants – “Beach House”

(Season 2, Episode 12)

Like #9 on the list, Holt is the straight man who then sends the joke over the top. But in this case, it’s how the camera undercuts his persona that draws the laughs. Jake is working overtime to prove that Holt has spilled his soup and surreptitiously removed his stained pants in his office. While most attempts fail (thanks in part to Holt’s encyclopedic knowledge of Yo-Yo Ma’s touring itinerary), Holt finally admits the truth to Jake to get him to stop — only for Jake to immediately spill hot soup on his own pants while celebrating. When Detective Amy Santiago (Melissa Fumero) finds Jake sitting weirdly close, behind Holt’s desk, we get the crowning image: Holt and Jake in their boxers, as Holt coolly assures Amy there’s “no story here.” Holt’s commanding and composed presence is firmly in place, but the camera hilariously upends it, letting us in on the secret foolishness of his position.

7 Podium Prank – “Sicko”

(Season 6, Episode 17)

While the first two entries on the list lean on Holt’s no-nonsense demeanor, this one plays on that dynamic only to explode it. Before the morning briefing, Jake plans a prank on Holt. The squad (but mostly Amy) is concerned for Jake’s well-being in the face of Holt's expected wrath, and he ratchets the prank all the way down from giving Holt ink-stained hands to just moving his podium a half-inch to the left. Jake doesn’t think he’ll notice, but we in the audience expect him to clock it — and we expect him to be furious. What we don’t expect is a full-throated, head-thrown-back howl of laughter and unbridled joy as Holt exclaims “You’re crazy! How did you pull this off?!” While maintaining and drawing laughs from his fastidiousness, this cold open undercuts our assumptions and reveals a delightfully unexpected side to the captain.

6 Power Walking in Florida - “Coral Palms, Part 1”

(Season 4, Episode 1)

The Season 3 finale of Brooklyn Nine-Nine left us wondering how Holt would adjust to life in the witness protection program in sunny Florida. Season 4’s cold open answered that question: by joining the neighborhood ladies for their regular power walk-and-gab session. He’s still himself — a pharmacist is no doctor, he insists — but he’s working hard to maintain his cover. He makes catty jokes, charms his neighbors, and claims he only knows Jake because of issues with their shared fence. It’s a witty twist on our expectations that undercover-enthusiast Jake is struggling while creature-of-routine Holt is thriving. And if you ever need a pickup line, consider Holt's distressingly side-spitting lament for his alter-ego’s beloved late wife: she was a “strong, female woman, with nice, heavy breasts.”

5 Holt Zings Wuntch – “Stakeout”

(Season 2, Episode 11)

Captain Holt was known for sobriety and maturity, sometimes to a fault. The one consistent chink in that staid armor? Deputy Chief Madeline Wuntch (Kyra Sedgwick), Holt’s nemesis, NYPD boss, and the only person who can puncture Holt’s propriety. Before receiving a medal, Holt tells Jake and Detective Rosa Diaz (Stephanie Beatriz) that he’s been up most of the night planning his sick burn: “Wuntch time is over.” The unimpressed and frankly concerned Jake and Rosa convince Holt to say nothing. Holt agrees: “I should be the bigger person! That shouldn’t be hard, given that Madeline’s not technically a person.” But when the time comes to maintain a dignified silence, he can only hold it together for so long. “Boom, did it!” Holt jubilantly shouts after delivering the zinger he’s so proud of. “Had it both ways. No regrets.” The long-boiling animosity between these two is one of the show’s best running gags, and a terrific opportunity to let the buttoned-up Holt access a pettier, surprisingly ruthless, and always hysterical side of his personality.

4 Holt Eats a Marshmallow – “Mr. Santiago”

(Season 4, Episode 7)

This episode depends on our assumptions about Holt and his “lack of flair,” according to Jake. Each squad member in turn imitates Holt eating a marshmallow for the first time. Most stick with the expected: a monotone, overly academic, disdainful description of the treat’s properties. When Holt enters the break room and takes the offered “marshed mallow,” his response is unanticipated: a gleeful, elfin giggle that was anticipated only by Detective Charles Boyle (Joe Lo Truglio). Holt's childlike mirth is a brand-new color for the captain, and it has us giggling right alongside him.

3 Hot Damn! – “Jake and Sophia”

(Season 2, Episode 6)

This cold open earns a top-three spot for giving us one of the most quotable and gif-able Holt moments of the series. When Amy is one minute late to work, the squad takes turns imagining what tragic and outrageous catastrophe has befallen her. Like Charles’ marshmallow giggle, Holt wins the game with the outlier entry: “I’d say she’s… in line at the bank. This is fun!” When Amy admits it, Holt responds with a clap, a triumphant fist in the air, and an explosive shout of “Hot damn!” For cool-as-a-cucumber Holt, whose affect remains steady whether he’s deliriously happy or devastated, this explosive celebration is a surprising and hilarious turn, and all the more funny (and true) for being rooted in something as low-stakes as a bank line backup.

2 Secret Handshake Extravaganza – “The Bimbo”

(Season 6, Episode 13)

When Jake is late to a morning meeting for the umpteenth time, Holt promises to break him of that six-year bad habit. As a punishment, Holt reveals that he’s invited the entire squad, except for Jake, to build an “intricate personal high-five." Holt may hate high-fives — “every minute of it was hell” — but he hates tardiness more. And so he dismisses the squad to receive their handshakes one at a time as distraught Jake watches from the table. In a giddy stream of physical comedy, Holt offers butt bumps and wiggles, a snake charmer routine, and an air guitar “Pete Townsend strum” complete with rock-star pursed lips. Even Leonard from Xerox gets one. It’s a dizzyingly funny collection of gags that perfectly showcase Braugher’s scalpel-like precision for both Holt’s characterization and physical comedy.

1 The Oopsie Doodle — “Unsolvable”

(Season 1, Episode 21)

Some of these cold opens have thrived on surprise, while others have pivoted on Holt’s firm, no-nonsense implacability. This one earns the top spot for combining both into one of the show’s greatest jokes. When Holt comes into work with a wrist brace, the squad (led as ever by Jake) tries to guess how it happened. Holt orders everyone back to work with an unremarkable explanation, only to then saunter over to Jake and conspiratorially offer him the truth. While scrolling through his camera roll to display a series of delightfully silly images, he calmly tells the detective “I was hula hooping... I’ve mastered all the moves: the pizza toss, the tornado, the scorpion, the oopsie doodle.” Jake — and the audience — are delighted by the almost unimaginable surprise of seeing and hearing about Holt performing anything at all called the “oopsie doodle.” But then, to Jake’s horror, he deletes all the pictures with a deadly calm, assuring Jake that “no one will ever believe you." And with a long, penetrating, gloating look, he closes the chapter on one of his most unexpected, devious, and gut-busting gags.

Brooklyn Nine-Nine is currently available to stream on Peacock.

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