Cuphead Wiki

Sheriff Esther Winchester is one of the new bosses from the DLC, fought during High-Noon Hoopla. Her level takes place in a desert plain. She was first revealed in the Game Awards trailer, and is the first and only shoot-'em-up boss in the DLC (although the gang fights her on the ground, or rather, near the ground). She is also the guardian of the Western Plains of D.L.C. Island and the keeper of the Desert Limes.



Esther has the usual western apparel for cowboys and cowgirls, while also being a cow in her entirety. She has a puff of curly hair, white horns, and a big snout with two gaping buck teeth. She wears a light blue hat with a pink flower for decoration. She wears a red bandana around her neck, a yellow shirt, pale yellow gloves with tassels, a red belt with a golden buckle, light blue trousers with white woolly chaps, and a pair of yellow boots with spurs. During her third phase, her body is turned into sausage links although her facial features and horns remain intact and her clothes are torn at the arms and legs.


Esther Winchester is shown to be wily and energetic, as she hardly stops smiling during her boss fight, seemingly having a lot of fun. She also displays childishness, as she blows a raspberry at the player while pulling out her vacuum. This behavior is further displayed in the DLC's ending, where she's seen swinging on a chandelier while snagging a meatball from a plate of spaghetti that Chef Saltbaker is carrying during his community service, indicating that she is a bit of a prankster. As evident by the vocalizations and mannerisms seen in her death screens, she speaks using a stereotypical western accent. She is also shown to at least have manners, despite her wily side, as evident by the fact that she is seen without her hat while in her saloon, indicating that she was following the custom of removing one’s hat while indoors. She also seems to be conscientious, as evident by her “watchful eye” on the Western Plains, which was mentioned in the Release Date Trailer.



Esther Winchester pops out of the saloon window, swings her hat around, and yells, "MooOOO Haw!" before the battle commences.

Phase 1[]

"Y'all took quite the fall...I s'pose it's last call!"
Esther Winchester, Phase 1 Death Screen

Death card mugshot cowgirl ph1

During this phase, Esther Winchester is capable of moving up and down between the door and top floor window of the saloon, which changes how some of her attacks play out (though she is always at the top floor window at the beginning of the fight). The first time she moves from the top floor window to the door, she removes the wanted poster of her on the ground floor window where her left arm sticks out, causing it to fly off. Her attacks in this phase are:

  • Esther pulls out 2 bottles of snake oil and shoots one oil pellet from each. These pellets fly halfway the distance to the player from their bottles on either side of them before making a U-turn and flying back to the right. When they hit the edge of the screen, they turn into two black, oily, snake-like creatures that fly at a faster rate back towards the player. Their preset path is to fly above and below the player, meaning these entities can be avoided fairly easily by flying forwards, in-between them. In Simple Mode, they are fired at a slower rate, travel slower, and are further apart. In Expert Mode, they fire at a faster rate, travel faster, and are slightly closer together.
  • Esther can also throw out a lasso, shout "Yee-haw!", and rope in a colossal cactus that stays on screen for a few seconds before she eventually lets go (possibly since these cactī will resist the strain with all their might). This cactus takes up either the top or bottom half of the screen, forcing the player to retreat to the unoccupied half. In Simple Mode, there is a larger amount of time between her shouts and the cactus being roped in, giving the player more warning.

Throughout the battle, small, flying horses will travel from the right-hand side of the screen over towards the left. Before they disappear offscreen, they will spit a spiky cactus ball at the player, which is sometimes pink and can be parried. They will always appear on the level of the saloon that Esther is not occupying. They will die if shot enough times, and in Expert Mode, they are faster, their speed making them harder to dodge or kill.

A vulture will also appear from the top left-hand side of the screen and drop a dynamite stick. Upon hitting the bottom edge of the screen, the stick will splits into three, then two smaller sticks, which travel upwards in waves. Do note that unlike most minions, the vulture cannot be defeated. In Simple Mode, the dynamite explodes into three sticks only. In Expert Mode, it explodes into a wave of four sticks, then a second one of three.

After taking enough damage, Esther will open the roof of her saloon with a vacuum in hand and blow a raspberry at the player. She will then take the roof off completely and begin running backwards with the vacuum, sucking up what remains of the saloon, commencing the next phase of the fight with her. Hitpoints = 675/513/576

Phase 2[]

"I've prepared y'all a tomb...right inside my vacuum!"
Esther Winchester, Phase 2 Death Screen

Death card mugshot cowgirl ph2

Esther has two attacks in this phase. In the first one, she sucks up many valuables (gold coins, wads of cash, coin bags, gold bars, and sheriff's badges) with her vacuum cleaner, also dragging the player towards her in the process. These valuables will appear all over the screen, forcing the player to move backwards to avoid them. In Simple Mode, the valuables are sucked up slower, giving the player more time to avoid them. In Expert Mode, she ends this attack more quickly.

After she sucks up enough valuables, Esther will duck down and make her vacuum shoot safes into the air, which rain down from the top of the screen. They are destroyed upon hitting the ground, producing gold bars, wads of cash, and coins, which all fly towards the player. Some of the items produced from the safes that she fires can be parried, telegraphed by their pink aura. In Simple Mode, the safes and the valuables travel slower and there are less of them. In Expert Mode, the safes fall slower.

After she takes enough damage, Esther gets a shocked expression as her vacuum malfunctions. The vacuum will then proceed to turn against her and suck her into itself, after which it transforms into an old-fashioned ACME steam cooker. It explodes, and we find out that the cartoon cow has now been processed into sausage links as she looks in a mirror before she realises her mistake and throws it away. She starts running backwards on all fours with her hat on her backside and her clothes ripped, either from the heat of the vacuum's innards or the process of turning her body into sausage links. Phase 3 then begins. Hitpoints = 833/855/960

Phase 3[]

"Let's be franks here, I'm yer wurst nightmare."
Esther Winchester, Phase 3 Death Screen

Death card mugshot cowgirl ph3

Esther Winchester starts this phase on the ground, though similar to the first phase, she is now once again capable of attacking from both the ground and above, flapping her "arms" when she flies and simply running backwards while on the ground. Wherever she is, she will spit steaks at the player that travel to the left in a looping pattern. If Esther was on the ground, the steak pieces will loop up in standard loop-de-loops, whereas in the air, their path is an inverted variant. Sometimes, the steaks can be parried, telegraphed by a pink aura. In Simple Mode, they loop in a smaller radius, making them easier to dodge. In Expert Mode, she will spit them out more rapidly.

Throughout this quarter of the battle, cans of beans with propellers on the opposite face to their opening side will fly across the screen. Depending on which way the cans are opened from, strings of beans will hang up or down to reach the player if they're in range. In Simple Mode, less cans of beans appear. In Expert Mode, there are more of them.

After taking enough damage, Esther will fly into the air and yelp before her body splits into separate sausages. These sausages will fall into a levitating tin can labelled "Prairie Dogs" that contains a picture where Esther is holding a plate of frankfurters. In Simple Mode, the battle will simply end in this phase as she stays in the air, shocked as her body twitches. Hitpoints = 742/713/800

Phase 4[]

"A gal can-tin-joy a moment's peace without you meddlin'."
Esther Winchester, Phase 4 Death Screen

Death card mugshot cowgirl ph4

A hole will open from inside the tin can that Esther was stuffed into after she was beaten in the previous phase, releasing 2 long chains of sausages. The hole's location coincides with the frankfurters' area on the picture. The sausages will float up and down the screen in a sideways V-shape, occasionally criss-crossing between each other, with gaps in their chains that the player can slip through to avoid damage. In Expert Mode, there are less gaps.

While this is happening, the picture of Esther on the tin can will spit out four or five jalapeños in a spread shot pattern. Most of the time, one of the jalapeños will be pink and can be parried. In Expert Mode, she will spit out five or six peppers.

If the player attempts to stay at the top of the screen, above the tin can and out of range of the two attacks, a can of beans will fly across this area, resembling the ones from the previous phase, discouraging them.

After taking enough damage, Esther will be defeated at the end of this phase. The tin will begin its death animation, expanding and contracting and appearing more damaged. The can's lid will also have vanished, allowing the individual sausages that it held to float upwards as angels, some holding a hat or a banjo. Esther's face on the can will also no longer be smiling. Her tongue will be hanging out of her mouth and her eyes will have crosses over them in place of pupils. Hitpoints = 769/864

Sound Effects[]


Unused Content[]

In the first phase, an UFO hovers over the player and moves left and right, shooting three Jareeds which spread out, one of which can be parried. It can be defeated, causing a new one to spawn in from the right-hand side of the screen.

This attack may have been reworked into the vulture, as the idea has already been used by Hilda Berg. The inspiration likely came from cows being abducted by UFO tracer beams being a common trope.


When Esther vacuums up valuables in the second phase, some can already be parried, as seen in the Game Awards Trailer when she was first shown and during the Nintendo Direct announcement shortly after. This has been changed in the release. Now, only valuables produced by the falling safes can be parried, which is limited to gold coins and wads of cash.

In the codes, the third phase is referred to as "meatball", and there is an unused phase called "Tbone". Only her fourth phase is named "sausage". The developers may have originally planned for Esther to either transform into different foods made from beef, similar to Hilda Berg's constellations. Or, she simply may have had more phases before becoming sausages takes up the focus of her remaining phases.


Regular Mode Expert Mode
How_To_Beat_Esther_Winchester_NO_DAMAGE_(A+_Rank)_-_Cuphead_DLC How_To_Beat_Esther_Winchester_on_EXPERT_MODE_(S-Rank)_-_Cuphead_DLC


  • She is the only shoot-em'-up boss besides Phear Lap that has actual ground. Dr. Kahl's Robot, while landborne, does not have any visible ground.
  • The attack where she sucks up valuable items is very similar to Djimmi The Great's attack in phase one where he launches a large number of gems and treasures from his box randomly, but reversed.
  • Sheriff Winchester actually first appeared in the book Cuphead: Cartoon Chronicles & Calamities. However, she had a slightly different appearance.
  • She is the only boss who does not have a complete circle in her second phase death screen because she is sucking it up with her vacuum cleaner.
  • In the sense that she is using it in her first phase, “Last Call” is a term used by bartenders to inform bar patrons that the bar is closing soon.
  • Her phase 2 attack can be a reference to the phrase “cash cow”, which is a product or business that keeps making a lot of money easily.
  • Her phase 3 death screen quote contains two puns, with the first being on "beef franks", which is a slang term for hot dogs, and "frank" as in "honest." The second one combines the phrase "your worst nightmare" with "wurst" which refers to "bratwurst", a variety of German-made sausages.
  • During her final phase, Esther makes a pun on the verb "can't enjoy" and "tin cans."
  • Her name "Esther" is pronounced similarly to "Winchester", which is the suffix of her surname.
  • So far, she, Beppi The Clown, Baroness Von Bon Bon, Sally Stageplay, The Phantom Express, The Devil, Moonshine Mob, and Chef Saltbaker are the only bosses to have four phases outside of Simple Mode.
  • She is the second boss to be turned into food. The first is Wally Warbles.
    • However, Esther is turned into food in the middle of her fight, whereas Wally gets turned into food after his fight and whether that actually happened or not is unknown.
  • During her lasso attack in her first phase, Esther's arms appear to clip through the windows of her saloon.
  • There was a bug where Esther would be stuck at Phase 2 when she hits the threshold and swapping her attack at the same time. This is fixed in Patch 1.3.3.
  • With Esther, there is a case of anthropomorphic inconsistency. Case in point, there is a little ranch of dairy cows in the background of her boss fight, however, she appears to be the only humanoid cow, whilst the others are just ordinary cattle.

Inspirations and similarities[]

  • She appears to bear a strong resemblance to Clarabelle Cow from Disney's Mickey Mouse franchise.
  • She could be named after a food brand known as Winchester Beef, an incorporated community in Texas, and a firearms manufacturer that makes rifles.
  • Her attack using snakes made of oil might be a nod to the term "Snake Oil", which is a type of phony medicine, as well as a catch-all term for a fake idea or a faulty product used to make money off gullible people.
  • The fact she is able to fly in her sausage form could be inspired by the Worms from The Forest.
  • Her quadrupedal running animation in her third stage and the face she makes when spitting out steaks appear to be inspired by the Queen-turned-to-dragon from the 1933 Betty Boop short "Snow White".


External Links[]

Inkwell Isle One
The Root Pack (Sal SpudderOllie BulbHorace RadicheChauncey Chantenay) • Goopy Le GrandeHilda BergCagney CarnationRibby and Croaks
Inkwell Isle Two
Baroness Von Bon Bon (Lord Gob PackerKernel Von PopMuffsky ChernikovSargent Gumbo GumbullSir Waffington III) • Beppi The ClownDjimmi The Great (Cuppet) • Grim MatchstickWally Warbles (Willy Warbles)
Inkwell Isle Three
Rumor Honeybottoms (Security Bee) • Captain Brineybeard (The Ship) • Sally Stageplay (Sally's Husband) • Werner Werman (Katzenwagen) • Dr. Kahl's RobotCala MariaPhantom Express (Blind SpecterConductorLollipop GhoulsHead of the Train)
Inkwell Hell
King Dice (Tipsy TroopChips BettiganMr. WheezyPip and DotHopus PocusPhear LapPiroulettaMangosteenMr. Chimes) The Devil
Inkwell Isle Four
Glumstone The GiantMoonshine Mob (Charlie Left LegsLight BugAnteaterAnnouncer Snail) • The Howling Aces (Pilot BulldogYankee YippersSergeant O'Fera) • Mortimer FreezeEsther WinchesterChef SaltbakerAngel and Demon
The King's Leap
The PawnsThe KnightThe BishopThe RookThe Queen