Darkwing Duck version

 When Darkwing needs to find out from he fearsome five (all minus Negaduck have been captured) what they are going to do with the emerald eye  of 
quatzequatel . So, he decides he needs to be sent to prison to find out. He made three supervillian personaes: which were Jumping Quack Flash, Roller Duck  and Demolition Duck.  
 
 His last personae he tried was Demolition Duck. This character had a mowhawk and a badboy air. "Why do brave men flee this shadowed form? Who is this dark mysterious figure? He's the mighty mallard menius....Demolition

Duck!" While this personae seemed to be the most sinister o f all three,  he actully saved a store from two robbers (not on perpose, just opened the door at the wrong time...). One of the store-members even goes on to sa y that, "that's what this city [ St. Canard] needs, a new hero to replace that ridiculous Darkwing Duck."  
 
 After all these personaes failing, he gives up. However, however, following giving up, he bumps into some St. Canard Police Department officers who did not take it kindly to j-walkers (namely Demolition Duck, a master of terror trust me, who was accidentally doing so), so they send him to prison. They were skeptical he should go to the supervillian prison, but after showing them his "scary" hand shadows they send him.

 
 
When Darkwing is sent to the supervillian prison, he encounters the Fearsome Four:
  "oh course I look familiar! Demolition Duck over here! The mallard minous, Champion of chicanery, Vangard of Villiany!"-- Darkwing Duck
"He's so arrigant!"-- Bushroot
"So 100% egotistical!"-- Liquidator
"So pretentious!"-- megavolt
"So, oh, springly!" -- quackerjack
"He must be...Darkwing Duck!"--fearsome four
 
There, he watches as Negaduck take all the fearsome five's powers. However, with the help of the fearsome four, he is able to defeat this Mega-Negaduck. He never used the any of the personaes again.
 

Alternate Darkwing Comic Version

The Three personaes he used in the episode were seen as some of the many Darkwings of the Multiverse brainwashed by Magica De Spell and Negaduck. It is unknown whether these characters are good or bad or just like the costume.