Quackerjack

Quackerjack is a recurring villain in the Darkwing Duck animated series and comic books. A former toymaker, he turned crazy and adopted a jester appearance, with an arsenal of deadly toys at his command. He's also one of Negaduck's Fearsome Five.

Background
He was once a toymaker who was put out of business after the "Whiffle Boy" video game market expanded. Understandably, he has a particular hatred of "Whiffle Boy" video games and toys. He became a supervillain who robbed banks to get money to fund his toymaking ventures and uses his toys to aid him for his crimes in most episodes. However, he's a genius who has built many successful toys. His catchphrase is "It's PLAYTIME!"

Quackerjack seems to be influenced by the classic clownish archetype of supervillain that includes the Joker, the Trickster, Punch and Jewelee, the Harlequin, the Prankster, Toyman, and the Clown. He also has a doll named Mr. Banana Brain (a parody of Mr. Potato Head), whom he carries around and talks to. Generally, he adapts a high pitched voice to have the puppet talk back in rhyming form. Other dangerous toys used by Quackerjack are a Giant teddy bear robot which destroyed a "Whiffle Boy" warehouse before self-destructing; a giant "Crying Crissie" doll with which he tried to unsuccessfully flood "Whiffle Boy" town, a pair of robot chattering teeth, an apathy causing toy called Mr. Relaxatron and his most fiendish torture device- - Mr. History, a talking trivia doll which repeats useless historical facts endlessly over and over!

Most times Quackerjack works alone, but he has been known to team up with Megavolt, and was a member of the Fearsome Five (led by Negaduck and including Bushroot, Liquidator, and Megavolt). His superpower is his "wackiness," which hardily annoys Negaduck.

Personality
Quackerjack was originally a deranged toymaker whose toys were dangerous and defective, and his company ended up getting shut down. He went over the edge and turned to a life of crime, driven by what he calls his "wackiness" to rob banks and cause chaos for a twisted thrill.

He keeps a toy he calls Mr. Banana-Brain, talking to it and making it seem like it's talking.

Ever since Negaduck destroyed Mr. Banana-Brain, Quackerjack went even further over the edge and became more of a terroist and sadist than before. However, this was also due to everyone stealing his ideas for toys and he started becoming more insane then ever.

When Quackerjack was reunited with his original Mr. Banana-Brain, he began to show remorse for what he had done and committed suicide by changing himself into a lifeless doll, believing it was the best thing he would ever be.

Powers and Abilities
Like Negaduck, Quackerjack possess no superhuman abilities, though that makes him no less dangerous than any other villain. While no martial artist, Quackerjack is incredibly athletic, capable of performing perfect backflips and impressive leaps. In fact, his acrobatic affinity and use of lethal gadgets makes him a top tier villain, also, his madness makes him highly unpredictable.

Darkwing Duck
Quackerjack is a brilliant toymaker, but all his creations tend to be dangerous, cleverly-disguised weapons, or tools he uses to escape. His trademark toy is chattering teeth that bite. Otherwise, he's used a number of toy or joke-based weapons and gadgets, like pogo-sticks, electric joy buzzers, and more.

Quackerjack once even invented a time-machine called the Time Top (due to its design being based on a spinning top).

His debut was in "Whiffle While You Work", in which he first met Darkwing (though he seemed to know him from somewhere, Darkwing didn't know him) and their rivalry was established.

In "The Haunting of Mr. Banana Brain", he stole a haunted jack-in-the-box that contained a demonic entity named Paddywhack, who possessed his doll for a little while, and fed on the emotion of suffering that he causes others. Quackerjack noticed a change in the voice of his doll (Paddywhack's voice was far deeper than the high pitch Quackerjack used for the doll himself), but seemed unsurprised that the doll was moving and talking under its own power. This means Quackerjack likely is not aware of the doll lacking life of its own (though he seems aware that it is a doll), suggesting insanity and draws a parallel to Batman's almost contemporary villain the Ventriloquist (created in 1988, only three years before Darkwing Duck). In the episode, he was forced to team up with Darkwing Duck to get rid of Paddywhack, or submit to eternal torment specifically designed by Paddywhack with Quackerjack in mind: Paddywhack would fiendishly (from Quackerjack's point-of-view) force Quackerjack to adopt "normal" modes of behavior. This was raucously characterized by the depiction of Quackerjack dressed in a business suit.

In "Toys Czar Us", he forced the manager of a toy store to stock shelves with his personal brand of fun, despite protest.

In "Quack of Ages", he went back in time using his Time Top to eliminate the very first yo-yo. This anks to Darkwing's intervention, this ended in his accidental aiding of the invention of the yo-yo.

In "Time and Punishment", he used the top to travel into the future with Megavolt to discover more advanced toys. Thanks to an accidental kidnapping of Gosalyn, he turned Darkwing into the revenge-crazed DarkWarrior Duck.

As a member of the Fearsome Five, Quackerjack appeared in the episode "Just Us Justice Ducks". In a fight with Gizmoduck, it is revealed Quackerjack has false teeth (though this may have likely been a gag).

In "Stressed to Kill", Quackerjack teamed up with Megavolt again, and, using a toy called Mr. Relaxatron, the two had the city in an apathetic daze as they robbed it blind and caused mass mayhem. Throughout the episode, he constantly annoys Megavolt by calling him "Sparky".

A friendly, more gentle Quackerjack is seen as one of the members of the "Friendly Four" in "Life, the Negaverse, and Everything". He's still insane but more docile and actually has somewhat of a conscience, being he still makes toy weaponry but only to use against Negaduck while he gives normal toys to children.

He briefly appeared as a Fearsome Five member again in the episode "Jail Bird". When Negaduck stole the powers of the other four members, it was revealed that Quackerjack's superpower was "wackiness" (a euphemism for mania), without which he became depressed and whiny.

Goof Troop
In the episode Axed by Addition of the Goof Troop series, Quackerjack makes a cameo on Max's watch.

Darkwing Duck comics
In the series' comic book revival under Boom! Studios, Quackerjack's character was revamped. In the first arc, "The Duck Knight Returns", he became more evil after Negaduck destroyed his Banana-Brain doll. He worked for Quackwerks much to his joy since he can apply his ideas to the company, but then he really snapped after no one would listen to his ideas. He became the leader of the Fearsome Four (minus Negaduck), destroyed a Crime-Bot with his bare hands, and blew up buildings with exploding action figures of himself.

After he was carted away to prison, Quackerjack later escaped and, in the single-issue story "Toy With Me", got a device that would turn St. Carnardians into soulless little toys. It is revealed he has a girlfriend named Claire. Darkwing manages to stop his plan and make him think things through, but Quackerjack escapes and turns himself into a toy at Claire's doorstep (which could also count as a suicide), claiming its all he'll ever be.

In Boom!'s final arc, "Dangerous Currency", Quackerjack is revived after getting touched by the slime that Magica De Spell uses to take over Duckburg and St. Canard. However, this story arc was never approved by the Walt Disney Company and is not considered canon.

Canonically, Quackerjack is shown to have been resurrected in a one-page cameo in "Dawn of the Day of the Return of the Living Spud II: Army of Starchness", published in issue #8 of the continuation by Joe Books. He is shown watching a news report on TV while working on a plan he has in store for St. Canard's upcoming toy expo, obviously teasing the story that was planned for the next issue (which writer Aaron Sparrow has stated would have him and Megavolt teaming up again). Unfortunately, due to the comic being cancelled after that issue, it will never be shown what Quackerjack's plan is, or how he was turned back from a doll.

Darkwing Duck
Quakerjack appears as a boss character in the video game. Darkwing battles him at the end of bridge level.

DuckTales: Scrooge's Loot
Once a player equips the Inventor costume, they can use an attack where there is a Quackerjack-In-The-Box.

Trivia

 * In "Stressed to Kill," Quackerjack is shown to have the ability to speak German while under the guise of Dr. Heebie.
 * According to Flapping Terror's interview with Tad Stones, Quackerjack was intended to be a darker character, much like The Joker, but he ended up being written as a more silly, eccentric type villain, which Stones was disappointed with. This was changed within the 2011 comic series.
 * Some of Quackerjack's criminal ways are based on some comic book villains: Joker and Toyman. Similarly, the issue Toy With Me's cover was taken from the Batman one shot The Killing Joke, which gave some backstory and development to the Joker such as revealing him to have become the way he was due to a "very bad day."