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Cuphead: The Delicious Last Course: How To Beat Winchester

"Cuphead," the quirky run-and-gun shooter stylized after classic cartoons, was a massive hit upon its release in 2017 for both the Xbox One and PC platforms, garnering critical acclaim for its style, gameplay, and characters. The game is also renowned for its collection of difficult boss battles, and the recent expansion, "Cuphead: The Delicious Last Course," has added onto that list of baddies. And while gamers aren't expected to spend too much time trying to conquer the DLC, "The Delicious Last Course" has a few memorable showdowns, one of which is with Esther Winchester.


More commonly known simply by her last name, Winchester is the corrupt sheriff of Inkwell Isle Four and is encountered during the level "High-Noon Hoopla." Winchester is no slouch — she's arguably one of the hardest bosses to battle in "Cuphead" overall — due to her oddly-timed attacks and her three attack phases, which ramp up in difficulty as the battle goes on. So, what's the best way for players to dispatch this new foe?

Use Ms. Chalice

A new playable character named Ms. Chalice was introduced in "Cuphead: The Delicious Last Course," and she might be the key if you want to be formidable against the likes of Winchester. The new "Cuphead" character is actually considered by many fans to be overpowered due to her homing pojectiles, quick movements, and her attacks when flying an airplane, which is the vehicle you will be using against Winchester when the time comes to fight her.


While purists might have something to say against it, it doesn't hurt to use the tools "The Delicious Last Course" has given to you in order to defeat a powerful boss, especially when Winchester could take hours of trial-and-error otherwise. In this case, Ms. Chalice is the perfect selection before your grueling battle with Winchester and could save you tons of time and frustration. She also comes with extra health booth, allowing her to withstand a bit more damage.

Winchester's first phase is tricky

Beating Winchester pretty much all comes down to careful positioning. According to YouTuber JustoAllDay, it's recommended that players stick to the middle left of the screen during Winchester's first phase. While level with Winchester's head, shoot Ms. Chalice's triple-bullets at her to ensure that all three projectiles register. When she goes low, use the plane's bomb attack. Winchester's primary attack during this phase are her snake oil pistols, which shoot projectiles that move left, then right, then become ghosts, and then launch towards the player. Find the middle ground between the snake oil "bullets" and you should be fine.


Winchester will also make use of her lasso: She'll move to the lower part of the screen and yank a giant cactus, which can cause some serious damage. Whenever you see the lasso get pulled out, it's best you immediately go as high up the screen as you can. While Winchester is executing these attacks, also be wary of the tiny cactus-spitting "horse fly" minions that will fly out from her mobile saloon, as well as a vulture-like creature who will drop TNT.

Use your special attack in Winchester's second phase

The second phase of the battle with Winchester is absolute chaos. The evil sheriff will use a vacuum to suck up tons of objects (and you as well if you're not careful), then launch them back out, causing a hailstorm of hazardous objects that will deal considerable damage. In YouTuber CrankyTemplar's spectacular no-damage playthrough of the battle, they patiently wait for each piece of debris to come into view before carefully dodging them. That's probably the best move for players to copy.


It's also imperative that you continue attacking Winchester while dodging, taking care to stay a bit closer to the center of the screen. During the second phase is the best time to use your character's super ability. If you are using Ms. Chalice as recommended, this takes the form of a giant missile. It's best to use this ability when being pulled by the vacuum for maximum effect.

Winchester's final phase all comes down to movement

Once you've dealt enough damage, it's time for the third phase, in which Winchester becomes a backwards-running sausage (no, really). This phase is the easiest of the three. All you have to do is dodge a few projectiles, be it cans of beans or raw steaks. Keep peppering Winchester with attacks while avoiding the obstacles and eventually, she'll transform into a can of sausages that use chains of sausages and peppers as weapons. Look for gaps in the chain to pass through while remaining level with the can formerly known as Winchester to deal damage.


The bell peppers may give you a bit of trouble. Unlike the linked sausages, these pass through the middle of the screen. It's going to be hard to dodge these, so keep focusing on finding the aforementioned gaps in the sausage chain to avoid as many projectiles as possible. Eventually, after enough bullets and maybe one more super attack, the can of sausages will suddenly spit out a choir of angel sausages. And just like that, you've beaten one of the most creative, bizarre, and memorable bosses "Cuphead" has to offer.