Porkrind blackmails Cuphead, Mugman, Bendy and Miss Chalice to do deliver a secret package down at Ribby and Croaks' club 'The Fly Trap'', after their baseball breaks his window and threatens to sell it off. The gift inside is a pair of ticking, sparkly dance shoes for Ribby, meant to be a vengeance prank from Croaks.
But due to the kids having bad blood with Ribby and Croaks, Porkrind grants them disguises and alibis:
Cuphead (Patch-eye Pete, delivery boy/secret assassin)
Miss Chalice (Biff Macintosh, handyman/secret assassin)
Bendy (Boswell Lotsabucks, billionaire politician/smuggler)
Mugman (Talulah Piccolo, washed-up dancer)
Their delivery plan goes south as Talulah becomes obsessed with the shoes and Pete and Biff have to chase her down. Meanwhile, at the Fly Trap, Bendy indulges in the spoils/luxuries...until the real Boswell Lotsabucks, who is the fattest fat cat in town exposes him!
Although the delivery was a bust, Porkrind gives the ball back to the kids for their safety and to clear his conscience. But, karma does get to him as the dancing shoes go off and explode, destroying his shop.
The explosion is so loud that it catches the Devil's attention underground. He is appalled when he spots his son, Bendy hanging with Cuphead and Mugman, the thorns to his side.
However, he recognizes the fourth member, who turns out to be one of his debtors: Miss Chalice.
It is then when the Devil's desire for Cuphead's soul comes curdling back as he conjures up a plan to get rid of him once and for all!