Inkwell Isle Four is the home of Cuphead: The Delicious Last Course, the game’s DLC expansion. It holds 5 full bosses — Esther Winchester, Glumstone The Giant, Mortimer Freeze, the Moonshine Mob, and the Howling Aces — plus the four King’s Leap chesspiece champions (The Pawns, The Knight, The Rook, and The Queen). The DLC bosses are noticeably tougher than the base game: Esther Winchester reaches 3200 HP on Expert across 4 phases, and the Moonshine Mob totals 1455 HP (Expert) spread over 4 phases. All figures below are from cuphead-bosses.json.
Esther Winchester — 2850 HP over 4 phases
Esther headlines High-Noon Hoopla with 2250 / 2850 / 3200 HP over 4 phases — the highest DLC total. Her moveset is Snake Oil Shooters, Cactus Lasso, Suck Them Up!, and Sirloin Spit, and her parryable objects are Cactus Balls, Valuables, Steaks, and Jalapeño Peppers. Her phase three and four shift her into sausage-form attacks, so the 3200 Expert pool demands sustained accuracy through all four forms.
Glumstone The Giant — 1500 HP, the mountain that moves
Glumstone guards Gnome Way Out with 1150 / 1500 / 1700 HP over 3 phases. His moveset is Geese Xing, Hammer Slammer, Hat Cannon, Spiky Hats, Gas Clouds, Sack Toss, Drumstick Spit, and Bone Spit. Parryable: Gas Cloud, Gnome Puff (Simple Mode), Jumping Gnomes, Dinner Bell, and Blow Dart Bird. His stomach phase is counted as a third form, which is why the cache lists 3 forms alongside 3 phases.
Mortimer Freeze — 1650 HP in the ice palace
Mortimer Freeze rules Snow Cult Scuffle with 1350 / 1650 / 1850 HP over 3 phases. His moveset is Whale Slam, Icicle Drop, and Card Shot, and his minions include the Icicle, Winter Whale, Ice Cube, Twin Popsicle Bat, and Snow Cone. Parryable: Buckets, Cards, and Twin Popsicles. The 1850 Expert total is the DLC’s third-highest, behind only Esther and the Moonshine Mob’s upper bound.
The Moonshine Mob — a 1455 HP crime syndicate
The Moonshine Mob is Bootlegger Boogie’s boss and a four-member fight over 4 phases totalling 975 / 1255 / 1455 HP (Simple / Regular / Expert). The component values are:
| Member | Phases | HP |
|---|---|---|
| Spider Mobster | 1 | 495 |
| Light Bug | 1 | 495 |
| Anteater | 1 | 393 |
| Announcer Snail | 1 | 72 |
| Total | 4 | 1455 |
Spider Mobster and Light Bug are fought on all three difficulties. The Anteater (phase 3) and Announcer Snail (phase 4) only appear from Regular onward, so their two HP numbers are Regular/Expert — that is why the Simple total (975) is just Spider + Light Bug, while Regular (1255) and Expert (1455) add all four members.
Its moveset cycles Web Bomb and Fly Call (phase 1), Music Beam (phase 2), Tongue Lash and Scuffle Ball (phase 3), and Voice-Wave (phase 4). Parryable: Pesticide Gas, Moonshine Barrels, the Anteater’s Tongue, and Soundwaves. The Announcer Snail is the weakest link at just 72 HP.
The Howling Aces — 1600 HP of dogfighters
The Howling Aces fly Doggone Dogfight with 1100 / 1400 / 1600 HP (Simple / Regular / Expert) over 3 phases. The component values are:
| Pilot | Phases | HP |
|---|---|---|
| Fighter Pilot Bulldog | 1 | 608 |
| Yankee Yippers (total) | 1 | 272 |
| Chinook Pilot Saluki | 1 | 720 |
| Total | 3 | 1600 |
The Yankee Yippers only appear from Regular onward (no Simple phase), so their two HP numbers are Regular/Expert totals (59.5/68 each, 238/272 for all four). The Simple total (1100) is just the Bulldog + Saluki.
The Bulldog carries 660 / 532 / 608 HP, the Yankee Yippers 59.5 / 68 each (238 / 272 total), and Pilot Saluki 440 / 630 / 720 (plus a 680 / 777 secret phase). Parryable: Bone Tattoos, “BOW/WOW” Letters, Pink Ray Lasers, and Pineapple Grenades.
The King’s Leap chesspiece bosses
The King’s Leap is a chessboard gauntlet of four short champions, each with a tiny HP pool compared to the DLC bosses:
| Champion | Level | HP | Parry |
|---|---|---|---|
| The Pawns | The King’s Leap | 80 (each pawn 10) | — |
| The Knight | The King’s Leap | 200 | — |
| The Rook | The King’s Leap | 160 | Heads |
| The Queen | The King’s Leap | not cached | Cannons, Lion statues |
The Pawns open the board at 80 total HP (10 per pawn), The Rook sits at 160, and The Knight at 200. The Queen closes it, and while her HP is not stored in the cache, her parryable objects are Cannons and Lion statues. These four are tests of tight mechanical dueling rather than endurance.
- The boss roster guide ranks all 41 fights including these DLC entries.
- Came from Isle Three? The Isle Three guide covers the base-game finale.
- The parry guide lists every DLC parry object above.
- The expert mode guide shows Esther hitting 3200 HP on Expert.
- The tips-and-tricks guide covers DLC phase discipline.
- The common mistakes guide flags the Moonshine Mob component order.
How the DLC compares to the base game
Sorting the DLC bosses by regular HP — Esther 2850, Howling Aces 1400 total, Moonshine Mob 1255 total, Mortimer 1650, Glumstone 1500 — shows the expansion trades the base game’s single giant health pools for layered multi-target fights. Only Esther and Mortimer sit above 1700 HP on their own; the Mob and the Aces spread their totals across 4 and 3 components respectively. Against base-game benchmarks like Hilda Berg (2600) and Djimmi (2720), Esther is the only DLC boss that clearly out-masses the originals, yet the DLC’s phase density — Esther’s 4, the Mob’s 4 — makes every fight feel longer than its number suggests. The King’s Leap champions are the exception: their 80 to 200 HP pools are pure skill checks with almost no endurance element.
Where to spend your first DLC coins
Because the DLC bosses lean on parry objects — Esther’s Jalapeño Peppers, Glumstone’s Gnome Puff, Mortimer’s Twin Popsicles, the Mob’s Moonshine Barrels — a charm that extends parry windows pays off more here than on the base isles. The character cache confirms Ms. Chalice starts the DLC with 4 HP (one above Cuphead and Mugman’s 3), which is why she is the recommended DLC protagonist for learning these denser patterns.