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Toy With Me is the first of two stories published in Darkwing Duck Annual #1. Later reprinted as bonus content in the "Campaign Carnage" trade paperback, it is notably the only story in Boom! Studios' Darkwing Duck comic that was not illustrated by James Silvani.
The story opens in the home of Aloysius J. Mandelbaum, inventor of the Molecular Digitizer with which he created the Whiffle Boy series of video games. Having since been let go, Mandelbaum idly speaks of his past successes to a visiting houseguest, and how the company's new "World of Whifflecraft" MMORPG essentially drove him out of his old job. His guest, however, turns out to be the villainous Quackerjack, who turns the Digitizer on Mandelbaum and turns him into a wooden toy. After sharing a brief conversation with his recently-built doll "New NEW Mr. Banana Brain", Quackerjack cackles in anticipation of his plan to reintroduce Quackerjack Brand Toys to the world, at the expense of the video game-addicted residents of St. Canard.
Later, Darkwing Duck and Launchpad McQuack find Mandelbaum's wooden remains and take him to the tower lab for study. Darkwing muses that ever since his return, Quackerjack's crimes have been getting more ruthless and needs to be stopped before he can cause havoc with the Digitizer. Darkwing wonders if he could find someone who knows of the villain's whereabouts, but Launchpad points out that about the only thing Quackerjack spends time with is his favorite doll, whose name currently escapes Darkwing. After some time spent trying to remember its name, Darkwing finds Honker bidding on an online auction, where the original Mr. Banana Brain (rebuilt after Negaduck tore it up) is up for sale. Though Darkwing doesn't win the bidding, Honker finds him the location of the winner's home in St. Canard.
Elsewhere, a package has just arrived at Whiffle Boy Entertainment, and Quackerjack wastes no time in bursting out of the box and turning the Whifflecraft employees into toys. He then boasts his plan to those who remain: to hook up the Molecular Digitizer to the building's servers and turn every hopelessly-addicted Whifflecraft player into his new line of Quackerjack Toys. Should the staff refuse, they will be the ones transformed instead, and so they are forced to bring Quackerjack the servers.
Darkwing and Launchpad pull up to the house of the doll's winner, a young woman named Claire who invites them into her house for cake. Darkwing explains the situation to Claire, and she admits that she bought Mr. Banana Brain for her boyfriend, who is actually Quackerjack. While Darkwing is appalled, Claire explains to him that "Jacky" is actually a nice guy, or at least used to be. She then recounts the story of Quackerjack's time working for Quackwerks' Toy Department. At first he was excited for the job, but over time, he started feeling underappreciated for his work and began slipping into depression and anger over his ideas getting rejected and his co-workers getting all the attention. Unable to take the constant rejection, Quackerjack eventually snapped.
When Mr. Banana Brain arrives, Claire explains that she had hoped to reunite Quackerjack with his old friend so that he would remember who he used to be. Gosalyn then calls Darkwing and informs him of what is happening at Whifflecraft. Inspired by Claire's story, Darkwing agrees to help save Quackerjack from his own anger.
Back at Whifflecraft, Quackerjack is getting impatient for his servers and decides to zap a few employees to speed things up. As he chats with New New Mr. Banana Brain, Darkwing arrives with his usual introduction before suddenly pulling the old Mr. Banana Brain out. At first, Quackerjack calms down enough to put his newer doll aside, but the servers then arrive and he immediately throws "Grandpa Banana Brain" to the ground. While Darkwing is incapacitated by the toy-transformed employees, Quackerjack hooks up the Digitizer to the servers, unaware that the two Banana Brain dolls are sitting on the wiring and are being exposed to the electrical current.
The two Banana Brains suddenly grow to giant size and begin arguing and fighting with each other over Quackerjack's attention, with Old Banana Brain trying to get Quackerjack to remember how things used to be and New New Banana Brain driving the villain to continue with his plan. During the struggle, Darkwing takes the Digitizer and zaps the dolls back to normal, knocking Quackerjack out of the building in he process. However, he is nowhere to be found outside when Darkwing comes out to look.
With Whifflecraft safe, Darkwing talks with Launchpad about what he would have liked to say to Quackerjack: that it's not good to be a toy to your own anger, not when there's people thinking of you. At Claire's house, she is shocked to see a Quackerjack doll sitting on her doorstep. Having turned himself into a toy with a miniature Digitizer, Quackerjack sadly admits to Claire through an attached note that "This is the best I'll ever be."
- The cover art for the comic is based on the cover for the Batman comic Batman: The Killing Joke.
- This issue has a dark ending. Quackerjack turns himself into a toy, this would also count as committing suicide.