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The 8 Most Difficult Cuphead DLC Bosses

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The Hardest Cuphead DLC Bosses

What are the most difficult Cuphead DLC bosses?

Cuphead quickly became one of the most popular indie games in the world when it was released, thanks to its unique vintage style.

However, this style also lent itself to some very difficult boss fights that could keep players occupied for hours.

Today, we’re looking at the most difficult bosses introduced to Cuphead from the DLC and what makes them so hard to fight!


The Most Difficult Cuphead DLC Bosses

Each DLC boss on this list has been chosen based on their level of difficulty and how often players had trouble fighting them.

Fans may not agree on everything; however, most players agree that these bosses are the absolute toughest to beat!

So, let’s not waste any time and get right into our list of the most difficult Cuphead DLC bosses:


8. The King’s Leap

Hardest Cuphead DLC Bosses The Kings Leap

Kicking off our list is a series of fights known as The King’s Leap, which includes Pawns, the Knight, the Bishop, the Rook, and the Queen.

While each of these fights is separate, they all share a chess theme, and you can’t use any weapons or charms while in combat.

Instead, when fighting these characters, you will have to rely solely on parrying in order to come out victorious.

Although this makes fighting these bosses fairly straightforward, constant parrying is easier said than done.

Often, you will need to restart fights more than once in order to get through them, especially if you struggle to parry.

There are also additional mechanics that need to be accounted for as well, which serve to make these fights more complicated.

For example, when fighting the Bishop, you can only parry his attacks after blowing out all of the candles in the arena.

It isn’t just as simple as bouncing around and parrying, so you will need to pay attention to what each encounter calls for.

Of course, since Cuphead is one of the best multiplayer games of all time, you could always have a friend help you out with these fights as well.

However, if you have a solid grasp of the game mechanics and can time parries correctly, these bosses are challenging but not impossible to beat.

That said, they still deserve a place on this list, as many players have still struggled to get past them!


7. Glumstone The Giant

Hardest Cuphead DLC Bosses Glumstone The Giant

In Delicious Last Course, Glumstone the Giant is one of the first bosses you’ll encounter, and he can be really hard to get past!

Since he is an early boss, players often make the mistake of thinking he can’t be that bad, only to find out he is a serious threat!

Honestly, the first phase of Glumstone’s fight is arguably one of the toughest in the Cuphead DLC, and it can be incredibly frustrating.

Not only will you have to dodge incoming projectiles, but you will have to do so on constantly sinking platforms that force you to keep moving!

Oh, and Glumstone just drags a cat across the screen sometimes to eliminate safe zones just because he feels like it.

This first phase is a complete nightmare, and there is no time to stay still or catch your breath because you will be constantly dodging attacks.

Once the second phase starts though, you’re still not out of the woods because now you will be attacked from both sides of the screen.

During this part, Glumstone will start bouncing a ball across the screen using hand puppets, basically taunting you to try and stay alive.

Then there’s the third phase, where you literally take the battle inside Glumstone’s gullet, where you have to shoot his stomach.

While the last two phases are a bit easier than the first, it’s still easy to mess up, meaning you have to do everything all over again!

Glumstone easily stands out as one of the hardest bosses to beat in any of the best Xbox One games to play right now, and he’s frustrated many players!


6. Moonshine Mob

Hardest Cuphead DLC Bosses Moonshine Mob

The Moonshine Mob is up next, and they aren’t interested in playing nice — or fair, for that matter.

This is another multi-phase fight that is designed to keep players on their toes until the very end.

During the first phase of this fight, you will have to face off against a gangster spider who will constantly call in reinforcements to ruin your day.

He will also drop explosive web traps to give you fewer safe zones to retreat to because the reinforcements alone just weren’t enough!

Oh, and you will also have to contend with the “ant police” during this phase, which will sometimes show up just to spray you with deadly pesticide attacks.

If and when you manage to survive this phase, you’ll be treated to phase two, which is arguably even more difficult.

When this phase starts, a showgirl will drop a phonograph into the arena that, instead of playing delightful music, will shoot deadly rotating beams everywhere.

While you try and avoid the death beams, you will also need to dodge explosive barrels that will start dancing in from both sides of the screen.

Make it past these, and you’ll be treated to a giant anteater with an aggravatingly tiny hitbox that makes doing damage extremely tricky.

However, you can’t get too comfortable even after defeating the giant anteater because the secret fourth phase is ready with a fake knockout.

Although the fourth phase only has you battling the Announcer Snail, if you’ve let your guard down, you can easily be hit by a projectile and die.

Trust us, nothing is more infuriating than beating all three phases only to be surprised and killed by a tiny snail.


5. The Howling Aces

Hardest Cuphead DLC Bosses The Howling Aces

Up next, we have one of the coolest fights in the entire DLC, if not the entire game, though it also stands out as one of the most difficult.

In this battle, players have to balance on the wings of a biplane while fighting enemies flying around the screen.

What makes this particularly difficult is that you have an extremely limited amount of space to move around.

Plus, because the enemies are coming at you from every angle and constantly moving, hitting them can be incredibly difficult.

However, what makes this fight one of the hardest is the final phase, which rotates your screen, forcing you to adapt to a completely different perspective.

This phase is infamous for causing many players to die, both because it is unexpected on your first try and because it’s difficult to adjust to.

Essentially, this fight is one that you will need to do multiple times until you get used to how the final phase works.

Once you get comfortable with the screen shift, it will be a bit easier to complete the fight, though it is still nowhere near easy.

Even when you get used to the change in perspective, you will still need to deal with dodging all of the projectiles that the Howling Aces throw at you.

This boss fight has become a roadblock for many players, and it is definitely one that requires a lot of patience to get through.

But, if you can keep your cool and put in practice, it is possible to get past it in a handful of tries!


4. Mortimer Freeze

Hardest Cuphead DLC Bosses Mortimer Freeze

With The Delicious Last Course selling over 2 million copies, it’s safe to say that many players have enjoyed this DLC in full.

However, it’s also safe to say that a great many of these players have faced Mortimer Freeze and had to stop a second to rethink their strategies.

What makes this boss fight so tricky is that it starts out as a fairly traditional battle by Cuphead standards.

Sure, Mortimer Freeze is tough, but if you know the mechanics, he is fairly straightforward to face down.

There are no gimmicks like there are with the Howling Aces or The King’s Leap, so it lulls you into a false sense of security.

During the first phase, you will have to dodge projectiles while the boss floats around the screen.

When the second phase starts, Mortimer switches things up by summoning a towering snow golem who boasts a shapeshifting ability.

If that wasn’t bad enough, this snow golem also has incredibly erratic attack patterns that make it hard to prepare for.

Make it past the golem, and you’ll suddenly have to dodge around on rotating platforms while attacks roll in from almost every angle.

These last two phases are what really trip players up, and if you’re not expecting these tricks, you could be in for a nasty surprise.

That said, it is challenges like this that have helped make Cuphead one of the best Nintendo Switch games of all time, and fans can’t get enough!


3. Esther Winchester

Hardest Cuphead DLC Bosses Esther Winchester

Esther Winchester is up next, and this boss fight makes use of more bullet hell tactics than most main-game bosses.

This means you can expect this fight to be filled with incoming projectiles from every corner of the screen.

While other DLC bosses also use this tactic, Esther is by far the worst offender, and her projectile patterns are incredibly hard to dodge.

If that wasn’t bad enough, Esther also serves as this DLC’s only vehicle-based boss, which already makes her tricky to fight.

To make matters worse, this fight is long, and it has four different phases that you will need to last through.

During each phase, Esther will summon a series of increasingly devastating projectiles that you will have to dodge in your plane.

Even if you’re a player that is comfortable playing through these flying sections, you will struggle to stay alive here.

However, the final phase is the absolute worst, and it ramps the difficulty up to a whole other level!

During this section, you will have to dodge even more incoming projectiles while navigating into small safe zones.

The margins for error here are basically nonexistent, so you will need to do everything almost perfectly.

While it isn’t the most difficult fight in the Delicious Last Course DLC, it will certainly test all of your skills and patience!


2. Devil And Angel

Hardest Cuphead DLC Bosses Devil And Angel

Devil and Angel, also known as Angel and Demon, is a secret boss fight that you can unlock by solving the Graveyard Puzzle.

This fight is kind of disorienting as it starts with the Devil in front of you and the Angel behind you.

However, if you try to look at the Angel, it will morph into the Devil, as that is the enemy who will be dealing all of the damage.

You will need to constantly be aware of where the Devil is, but you can counter its projectiles by turning your back on them.

While this seems counter to typical mechanics, these projectiles won’t harm you, though you will need to be aware of where they’re coming from.

Once you’ve learned this gimmick, the boss battle isn’t too difficult, though the sporadic lighting clouds can still trip you up.

Really, the hardest part of the fight is finding a rhythm and keeping an eye on which direction the projectiles are coming from.

Although this is easier said than done, after a few attempts, it will become a lot easier to manage overall.

If you’re used to playing some of the best third-person PS5 games and watching things from all angles, you will also have a better shot.


1. Chef Saltbaker

Hardest Cuphead DLC Bosses Chef Saltbaker

Taking our number one spot is none other than Chef Saltbaker, the final boss of the Delicious Last Course DLC.

Even after facing down all of the other DLC bosses, it is still surprising how difficult Chef Saltbaker is to beat.

Starting off, this is the longest fight in the game, so before starting this battle, make sure you have a lot of time to kill.

There are also so many projectiles that you will probably start dying just because you’ll get tired of trying to keep track of everything going on.

Between the flames and the random sawblades that pop up, there is no time at all to take a breath and think about a strategy.

The only thing you can really do to get past this boss is practice, practice, and even more practice!

Be prepared to always have something new thrown at you, even while trying to dodge the last couple of projectiles.

During the last phase of the fight, things get a bit easier, as there are fewer projectiles, but you still need to get down a series of descending platforms.

It’s easy to slip up here simply because you’re tired at this point, so don’t let your guard down and get complacent!

While all of the bosses are tough, Chef Saltbaker is on a new level of nightmarish, and we’d be surprised if anyone beat him on their first try!



We hope you’ve enjoyed our list of the most difficult Cuphead DLC bosses and that we didn’t make you relive too much trauma!

Each of these bosses presents a unique challenge to gamers, which is part of the appeal of this great DLC.

Don’t let yourself get frustrated if you can’t get past some of these bosses on your first try, as we’re fairly sure no one has!

Here’s a quick recap of the most difficult Cuphead DLC bosses:

  1. Chef Saltbaker
  2. Devil And Angel
  3. Esther Winchester
  4. Mortimer Freeze
  5. The Howling Aces
  6. Moonshine Mob
  7. Glumstone The Giant
  8. The King’s Leap

Which of these bosses gave you the most trouble? Leave a comment below.

Shawna Schofield is a professional freelance writer and part-time YouTuber. When not writing or recording she spends her time playing Fallout, Elder Scrolls, and Dragon Age.

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