As seen in the introduction, Cuphead seems to have a somewhat greedy personality, apparently willing to risk anything to get what he wants, causing the infamous bet which he nearly cost him both of their souls. Despite his flaws, however, he seems to be kind-hearted and has good intentions overall, such as in the good ending where he and Mugman burn all the soul contracts, setting everyone free.

In the title screen and boss battles, he is seen with white gloves and brown shoes. This design was also used for his cameo appearance in Super Smash Bros. Ultimate, as both his costume and Spirit artwork use it. Cuphead loves his family and friends. He is very loyal to them, despite his flaws, and will do everything he can to protect them. In the casino, Cuphead and Mugman were on a winning streak at the Craps table. When the Devil came to the table, (which was a surprise for the boys) he offered a bet: if the boys won, they would get all the loot in the casino, but if they lost, the Devil would take their souls. In the beginning moments of a boss battle, Cuphead will hoist his pants, smiling, with determination on his face. The sole exception to this is the fight with The Devil, where he seems to be terrified, reusing the sprites Cuphead uses if he fails to stop The Spectre Syndicate from reaching The Legendary Chalice's urn in the Mausoleum levels. After the update, he may sometimes pump his muscles with a more determined grin.After each subject is defeated (except for the third one), the Baroness will appear from the gate of Whippet Creampup and shake her fist in anger at the player(s). The next subject then appears as Whippet rolls his eyes. The boss fight is also similar to that of Ado/Adeleine from Kirby's Dreamland 3/ Kirby 64: The Crystal Shards, as both bosses summon a series of mini-bosses (one by one) to battle the players before confronting them themselves. Bon Bon and Ado/Adeleine also both make an angry and frustrated reaction upon the defeat of each mini-boss. Mini Bomb - Shoots missles in a downward arc that do above average damage to the enemy but have a slow fire rate.

Whippet Creampup is a giant anthropomorphic strawberry flavored cake. On its sides, it possesses two towers made out of cake, which support eyes. It also has bars on its mouth. The top of its towers is made out of whipped cream. In these phases, although he’s one of the baroness’s minions, touching Whippet Creampup's body will not hurt the players.

While not immediately apparent, the Baroness was made to resemble a soda bottle, with her head acting as the bottle cap. After some training, Cuphead and Mugman went to go to collect the soul contracts, using their powers to battle bosses, run through levels, and save the Legendary Chalice. When travelling from Inkwell Isle One to Inkwell Isle Two, the Elder Kettle informs the boys that their strength is growing thanks to the power of the soul contracts, and soon it will be enough to defeat King Dice and even the Devil in battle. The way she wields her candy cane like a shotgun may be a reference to a scene from Adventure Time in the Candy Kingdom, in which a citizen grabs a candy cane and fires it at Finn while making shotgun noises. The baroness herself may also have in part been inspired by Princess Bonnibel Bubblegum.

In Simple mode, Bon Bon will appear to fire the candy cane shotgun endlessly without commanding Whippet Creampup to move, and the Jelly Bullies Squad will still be sent out. Also, in their simple KO, Bon Bon still cries like she does in regular or expert, but this time, instead of pounding its fists on the ground, Whippet Creampup will just sit still with a disappointed look in its eyes. Lobber- Purple orbs that bounce twice before popping. Does a lot of damage but has delayed shooting. In the E3 2015 trailer, Cuphead seems to pour a beverage labeled "XXX" into his head, though he is never seen doing this in the final version. This along with Mugman drinking his soul in his intro animation lead to the infamous theory that their heads contained alcohol. Made of porcelain: 3 hits can kill him (4 while equipped with the Heart Charm,5 while equipped with the Twin Heart Charm and 6 with the Heart Ring charm if Cuphead gets all 6 parries before getting hit).Upon the Devil's defeat, the boys accept his surrender and burn all of the soul contracts, releasing the residents from their eternal servitude to the Devil. The boys then went home and told the residents that they are now free from their debt. They are praised for their bravery, and an all-day celebration began. In their success, the boys promised to never get into trouble again—until the next time. Rapid Fire Bullets - The default bullets for the plane. Like the Peashooter bullets, Cuphead can shoot multiple bullets and they have a long range. Throughout the entire battle, there will be a moving platform resembling a piece of candy which players can stand on.

Super Bomb Transformation - As a Super Art, Cuphead can transform into a giant bomb that explodes either on impact or the if duration timer runs out.He may likewise have been influenced by the design of various sentient porcelain characters from the 1934 Silly Symphony The China Shop. Can't be resurrected without the help of Mugman (likewise, Mugman can't be resurrected without Cuphead).