10 Times Winston Was the Best Character on New Girl

Top 10 Times Winston Was the Best Character on New Girl

We don’t love him in spite of his weirdness. We love him because of it. Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Times Winston was the Best Character on New Girl.

For this list, we’ll be looking at some of the funniest and most memorable moments from New Girl’s Winston Bishop.

#10: Fruity Drinks
“Re-Launch”

Nick warned us that fruity drinks make Winston all weird. But while Nick finds this weirdness annoying, it just makes us love Winston more. Against his better judgement, he still gives in and makes Winston a fruity drink at Schmidt's rebranding party. Upon taking one sip of the drink, Winston gets hilariously loopy. Winston is already a pretty goofy guy without any help, but the fruity drink pushes him to extremes. He giggles like a little kid, continuously calls himself naughty for some unknown reason, and even starts spontaneously singing. It might have been Schmidt’s party, but Winston stole the show.

#9: Being Weird with Furguson
Various

Winston originally steals Furguson from a cheating girlfriend, and goes through a brief phase of wanting to kill the poor cat as revenge. So no one could have predicted that they would become best friends. Along his misguided journey to exact revenge on the completely innocent cat, Winston ends up falling in love with Ferguson instead. He is absolutely crazy about this feline. Apparently, he takes baths with him, eats with him, and even takes weekly selfies with him. The rest of the group may roll their eyes and look at him in confusion, but Winston’s bond with Furguson only proves how big of a heart he has. And it’s also just really funny.

#8: When He Didn’t Study for His Police Exam
“Girl Fight”

Watching Winston avoid studying for his police exam is like a master class in procrastination. Every student probably has some spectacular stories of putting their work off until the last minute, but Winston is so nervous for his police academy entrance exam that he gets seriously creative in the lengths he will go to put off studying. He fills his room with handmade paper snowflakes that are totally necessary right this second and he inserts himself into Nick's relationship with Kai. Coach has to tie him to a chair just to get him to buckle down and study.

#7: When He Had a Discussion with Schmidt About Race
“Cabin”

Like any great sitcom, “New Girl” occasionally discusses serious topics with a touch of humor. Schmidt worries about Winston not being able to properly express himself while having all-white roommates. So Schmidt takes it upon himself to try and allow Winston to be himself, and Winston schools him on exactly what that means. Through a series of hilarious encounters, Winston teaches Schmidt that having white friends did not make him lose his black identity. Winston tricks Schmidt into thinking that he wants to get drugs, and Schmidt goes so far as to invite a stranger into their car to buy some. The whole thing ends up being pretty funny, but it is nice to see Winston talk to Schmidt openly and honestly about race.

#6: When He & Cece Messed with Big & Little Schmidt
“Parents”

When Big Schmidt comes to town for Thanksgiving, Winston teams up with Cece to pit them against each other in a battle of manliness. They give them a series of ridiculous challenges to compete in for their own amusement. Though it is unofficial, this might be the first ever documented Classic Winston Cece Mess Around. Though these two have been acquaintances for a while, this is one of the moments that truly bonds them as friends. His goofy friendship with Cece, and this moment in particular where they manipulate the Schmidts to their whim, is first rate.

#5: When He Sang “Wicked”
“Fancyman, Part 2”

On a long drive to Mexico, Winston passes the time by singing along to the Wicked Cast Recording. Winston was all of us at this moment: alone in the car, singing as loud as he can, not caring how off key he is. Of course, Cece and Schmidt were hiding in the back of the car the whole time, but Winston didn’t know that. He just kept singing at the top of his lungs, passionately, and unashamed. We should all take a lesson from Brown Lightning here. You do you, Winston; sing like nobody’s listening.

#4: When He Was Cece’s Bridesman
“Bob & Carol & Nick & Schmidt”

We’ve already mentioned the special nature of Winston and Cece’s relationship. They’ve had a lot of great moments over the years, but this is definitely one of the best. It was extremely heartwarming when Cece asked Winston to be her brides-man, even though he was already one of Schmidt’s groomsmen. The moment proved just how much they really mean to each other. And even more heartwarming than Cece wanting him to stand by her, is just how excited Winston was to do it. This request holds so much more weight considering that just the day before, Winston had gotten Cece drunk while wedding dress shopping and helped her get saddled with the most ridiculous dress. But these kinds of shenanigans are just a staple of their friendship.

#3: The Crepe Pan
“Clean Break”

Schmidt is usually the sensitive one of the group, but this time Winston is the one who gets emotional when Coach is getting ready to move to New York with May. Coach expresses that he wants to make a clean break, leaving anything nonessential behind, but Winston tries to convince him to bring along some mementos - including a crepe pan that is important to both of them. Coach is pretty ruthless about his clean break routine and Winston gets more and more upset with him, but eventually he breaks Coach and the two burst into a crying fit about how much they will miss each other. The whole thing is pretty hysterical.

#2: When He Was Puzzling
“All In”

There's really no other way to say it other than that Winston gets super weird when he's puzzling. When he first starts, he treats it like it's some new mission he's embarking on that he has to spend a lot of time and energy on. Watching how annoyed Schmidt gets at Winston's incompetence is hilarious. Winston is so terrible that he doesn't even realize that a lot of the pieces he's using are just upside down, and he spends so much time working on it that he runs out of clothes and starts wearing a sweatshirt as his pants. But we can’t get as annoyed with him as Schmidt; after all, it turns out he’s colorblind. But also: his wonderful weirdness is exactly why we love him.

Before we unveil our top pick, here are a few honorable mentions.

His Honey Roast
“Big News”


Sympathy PMS
“Menzies”


When He Learned How to Use a Ruler
“Teachers”

When He Helped Nick with His Zombie Novel
“Eggs”


Theodore K. Mullens
“Secrets”

#1: Prank Sinatra
Various

According to Winston, he is the best at pranks. People even call him Prank Sinatra. But, according to the rest of the gang, he is the worst prankster ever. He always goes way too big or way too small. His obliviousness to his own ineptitude is exactly what makes his pranks so great. Whether it's releasing a badger at Cece's wedding, or putting a blueberry in Schmidt's cereal, his pranks are always hilariously awful. It’s okay Winston, you always made us laugh. And though he goes by many names, like Brown Lightning, Winnie the Bish, and Theodore K. Mullins, we will always know and love him as Prank Sinatra.