Sugarland Shimmy is a level on Inkwell Isle Two, where the fight with Baroness Von Bon Bon takes place. It is represented on the map by a muffin-shaped building. This is one of the three initially available levels on the isle along with Pyramid Peril and Carnival Kerfuffle. Once you defeat Sugarland Shimmy, you unlock Funfair Fever, Aviary Action!, and an NPC that looks like a cookie.
The level is set in a candy world, with lollipops and massive cakes. Whippet Creampup (Baroness' castle) stays constantly on the right, from where she sends her minions from. Once you reach the final phase of the fight the castle will start moving, chasing the player through the sugarland.
- During phase 4, parry Pasty Menthol (the peppermint the castle shoots out) to gain more cards for the EX-Move.
- Precise Parrying.
- Roundabout - Lord Gob Packer, Kernel Von Pop, Sir Waffington III, Sargent Gumbo Gumbull, Baroness Von Bon Bon
- Chaser - Kernel Von Pop, Lord Gob Packer, Sir Waffington III, Muffsky Chernikov, Baroness Von Bon Bon
Before the battle begins, Baroness Von Bon Bon will be standing in front of Whippet, with a giant candy cane. She'll proceed to use her finger to chop her head off (foreshadowing the final phase), then she'll be pulled into her castle will the candy cane.
This battle is very unique, because the first three phases are random. There are multiple mini-bosses that she'll send out. The mini-bosses in this level are Kernel Von Pop, Sir Waffington III, Lord Gob Packer, Sargent Gumbo Gumbull and Muffsky Chernikov. In Simple mode, you won't encounter Muffsky.
"How's the jaw, ol' chum?"
—Lord Gob Packer, Death screen
Lord Gob Packer is a giant jawbreaker, which will chase you around the map along with a tiny jawbreaker.
It is recommended to use the Roundabout or Chaser, because you're always running away from Lord Gob Packer. It's also recommended to run around in circles by using the given platform. If you ever get in any trouble, if you have the Smoke Bomb charm equipped, you are able to dash through Lord Gob Packer.
Once you defeat Lord Gob Packer, he'll stop, then crack into pieces. He cracks layer by layer, then revealing his head, which has cross eyes and a halo on top. He'll then fly to the top of the screen. This animation is very long, so you have some time to take a break after you finish him.
"For me, a sweet tooth is fiendishly uncouth!"
—Kernel Von Pop, Death screen
Kernel Von Pop is a giant candy corn. He'll go in an 8 like pattern, while sending out mini candy corns that'll fly up to the top of the screen.
It is recommended to dash or jump when he gets too close, and to stay away from him while he's airborne.
Once you defeat Kernel Von Pop, he'll fly up with his teeth being crooked. He'll look crazy, and his layers will jump off then back on.
"I chew 'em up and spit 'em out."
—Sargent Gumbo Gumbull, Death screen
Sargent Gumbo Gumbull is a gumball machine that'll run around the map. Occasionally, he'll spit out gumballs everywhere, which rain down onto the players. This is actually the easiest of the phases, so do not panic.
It's recommended to try to get close to him and use your Roundabout. Focus on the gumballs and dodge them, left and right. If you have the Smoke Bomb charm equipped, you are able to dash through him. You may use this if needed.
Once you defeat the Sargent, his head will explode and he'll run away.
"Straight off the iron and too hot to handle!"
—Sir Waffington III, Death screen
Sir Waffington III is a giant waffle with a butter hat and syrup wings. He'll fly around the screen, and occasionally split himself apart, hurting the player.
It is recommended to use the Chaser to get Sir Waffington III. Try to keep distance from it as much as possible, but do not get too close to the castle. In case it gets too close, expect it's disassembling to find a way to dodge.
Once you've done enough damage, Sir Waffington III will once again disassemble, but this time, it doesn't hurt you.
"Delicious and vicious, while maliciously nutritious."
—Muffsky Chernikov, Death screen
This mini-boss isn't played in Simple Mode
Muffsky Chernikov is a giant cupcake. He'll bounce around the map, and when he lands, little waves of icing will come out of him. Muffsky Chernikov is the hardest mini boss out of the five, explaining why he isn't played on Simple Mode.
It is recommended to dash through him when he's about to land near you. Beware of his splash damage. Note that you need to dash away quickly before his third bounce instead of sitting there waiting for it to land, as its skill of bouncing from walls is more powerful than Goopy Le Grande's.
Once you've done enough damage, Muffsky will look up at his cherry, which now has eyes. He'll start melting while his arms and legs are failing, then the cherry will explode, exploding Muffsky in the process.
During the fight, you'll only have to fight three of these mini-bosses (which count as three phases), but beware, since there are slight changes between these phases. During the first phase, you just fight the mini boss. During the second phase, you fight the mini boss while little Jelly Bullies run across the bottom. During the third phase, you fight the mini boss, little Jelly Bullies will run across the bottom, and Baroness Von Bon Bon will start to shoot cotton candy at you, which come in trios. Note that you can parry some of the Jelly Bullies and the pink cotton candy that she shoots in phase three. You can also shoot the Jelly Bullies while crouching for your own sake.
Phase four has Baroness Von Bon Bon order her castle to chase after Cuphead and Mugman. She'll throw her head over to the player while it happens. During this, peppermint will roll out from the castle, which can be parried.
During this phase, use the platform to your advantage to dodge the head and parry the peppermint to fill up your super meter or give you more movement.
After dealing enough damage, Baroness Von Bon Bon is defeated and she cries while her castle pounds it's fists on the ground. Note that you can only actually damage her by shooting her body, so it is best to use the Chaser for this phase.
However, this phase is very different in Simple mode, since Baroness Von Bon Bon would just shoot cotton candy at you instead of ordering her Castle. As they can be easily destroyed, just keep shooting, stay off the ground as you don't have to deal with the Jelly Bullies Squad.
[[File:|centre|thumb|330x330px|Music While fighting in this level]]