Top 10 Funniest Charles Boyle Moments on Brooklyn Nine-Nine

Boyle has always weirdly flexed on Terry Jeffords, despite Terry probably being able to crush him with a pinkie. When Terry finds out that Charles and Captain Holt are doing yoga together, Terry is a little hurt that Holt didn’t come to him for fitness help. Boyle again tries to put his bone strength over Terry’s muscle strength…in a typical Boyle way. However, after Terry hurts his back, Boyle proves the power of his bones by carrying him through the precinct in a surprising feat of strength that pays tribute to “An Officer and a Gentleman.”

After Rosa wears a pink shirt to work, the squad is incredulous, but keep it to themselves. Boyle is quite put out though, since none of them mocked her for it. He’s especially mad because they all mocked him for years by calling him “Mr. Grapes” after he wore a tie with a small amount of purple on it. Instead of convincing them of their hypocrisy, they instead decide to mock Boyle hypothetically wearing pink. Boyle’s exasperation and the squad’s juvenile mockery make this a relatable and funny cold open.

When Sal’s Pizza burns down, Jake is sure it’s arson and is determined to find the culprit. Boyle doesn’t think it’s worth getting into a conflict with the fire department over – unless Jake thinks it’s worth it. Despite Boyle’s tendency to suck up to his bestie, he’s also quick to correct Jake’s opinion on Sal’s being the greatest pizza in the area. Ever the food connoisseur, Boyle reveals he sends out a weekly email newsletter/blast about which local pizza is the best, using the usual criteria like sauce or crust, but also “mouth feel.” It’s a great scene that combines two of Boyle’s greatest loves – Jake and food.

Always out to please everyone, Charles accepts readily when Captain Holt asks that he join him to help win a squash tournament. However, Boyle is worried, since squash brings out his competitive side and makes him quite un-Boyle-like. Boyle manages to contain himself, but when they’re unable to match up to their opponents, Holt reveals he knows about Boyle’s wild side and asks him to – “unleash…the beast!” And unleash it Boyle does! Seeing the usually mild-mannered Charles go full-on competitive, with trash talking, breaking rackets, and even slapping Holt on the butt, is a laugh riot!

Boyle’s brief sexual relationship with Gina Linetti isn’t very healthy, but it’s fodder for some great comedy. After he accidentally records them together in the station’s camcorder, Boyle is desperate to get it back – from Hitchcock. Instead of money, Hitchcock demands something more difficult to acquire – getting Charles to make him seem cool. Boyle’s half-hearted attempts at this throughout the episode are hilarious, as he clears low bars like getting Jake to mention his name without mocking him and saying Hitchcock is handsome. Boyle must eventually wrestle with Hitchcock over the tape in the locker room, which sees them both wrapped around a bench. Talk about bending over backwards for a relationship!

Charles loves Halloween – all the squad do, but for very different reasons. Boyle always dresses up in costume (or ‘stume, as he calls it), yet the squad mocks his outfits, making wildly inaccurate guesses on what they are. Finally, Boyle decides not to dress up at all. However, he’s shocked to find that not only has the entire squad, minus Holt, dressed up for a change, but they also insist that they’ve never mocked him for his ‘stumes. Cue Boyle changing into an Elvis costume and returning, only to discover that they’ve all changed into street clothes and are right back to making fun of him. Even Holt gets in on it – though we’re not sure if it’s intentional. He’s hard to read.

This cold open sees the squad playing a rousing game of Boyle Bingo – Thanksgiving edition. In the game, they’ve all written down things they’re certain Boyle will say or do on Turkey Day. These include his festive spirit, facts about the holiday, and objecting to the game when he finds out about it. Honestly, we’re just surprised no one had “Boyle falls on the floor” for their card. The group mocks Boyle a lot, but this is one of the more good-natured ribbings they give him and shows just how well they know him. Plus, it starts the episode off with a bang. Or rather, a boom!

Charles hits things off immediately with Genevieve, a woman he meets at a courthouse. The only problem – she’s immediately put away for insurance fraud. However, Boyle is sure she’s been framed. When he and Jake interview her, Boyle’s comments are, as usual, very personal, and often gross. Except, Genevieve is clearly on the same wavelength. The three-way conversation between he, Jake, and Genevieve is gold. But it becomes a little too much for Jake, so he has to dip out. It ultimately ends up being too graphic for even the prison guards, who kick Boyle out. Disgusting they may be, but these two are perfect for each other, and hilarious to boot!

Charles Boyle is known for many things and one of his most frequently seen quirks is how often he makes unintentional innuendos. These include everything from referring to his wedding invitations as “STDs” to saying that he’ll go to any lengths to get his son his favorite toy in a…unique way. Everyone knows it’s just because he’s awkward and weird, but it’s still disconcerting for his friends and coworkers. Thankfully, we don’t have to hear it all the time, and Boyle’s inadvertent double-entendres always leave us satisfied – because we’re laughing so much.

Before we get to our top pick, here are a few honorable mentions:

Fax Machine, “USPIS”
Quite the Mental Image He Paints

Nancy Drew, “The Vulture”
Boyle Aspiring to Be a Teenage Girl Detective Explains So Much & So Little

Single Ladies Dance, “Lockdown”
Watch Out Beyoncé!

Fiber, “Into the Woods”
Boyle Looks Out For Jake’s Health Even in Serious Situations

Introduction, “Pilot”
Right From the Start, Boyle Was Full Boyle

The genius of this cold open cannot be overstated. Its beauty is in its simplicity. Jake arrives at work and asks Boyle how his weekend was. Boyle replies that he fell ill after watching “Bullets Over Broadway” … What follows is a long, long pause. Jake’s face is completely deadpan following the truly terrible pun, while Boyle barely contains his laughter before explaining the joke. It’s both actors’ favorite cold open and we can see why. Not only does it perfectly capture their character’s relationship, it’s also Boyle’s funniest moment on the show.