Darkwing Duck goes back in time with Gosalyn and he meets himself in high school when he was known as "Drakey". He then sees a record shop being robbed by Elvis look-a-likes. Due to Darkwing's inaction, Darkwing's present time world gets changed, so they have to straighten out the mess they made.
Drake Mallard stops off at a SHUSH hideout on his way to take Gosalyn to school. He changes into his Darkwing Duck disguise and takes the package inside. Gosalyn follows him, against what he told her to do, and while Darkwing is in the lab, Dr. Sarah Bellum shows him the reason for the delivery. He has a tape that has an encoded program that activates a time machine. As they are entering the room with the machine, Gosalyn hides in the back compartment of a golf cart. It turns out that the golf cart is the time machine and Darkwing accidentally starts it up and goes back in time. Gosalyn appears as they are traveling through time and they land in St. Canard in the time when Darkwing was a little boy. He his picked on by another little boy named Lamont who calls him Drakey. Lamont takes Drakey to the music store where they meet the gang and Lamont's big brother who uses his guitar, Cecil, to create a sound wave that breaks safes. They go back into present time and find things have changed. The crook that Darkwing didn't stop in the past is know king of St. Canard.
After a brief fight, Gosalyn and Darkwing get back in the time machine and return to the past to set things right. They just miss catching the crooks but they do run into Drakey. Gosalyn tells Drakey that Darkwing is a superhero. They get Drakey to lead them to the King's hideout and as they are spying on them, Drakey blows a bubble and it pops causing them to fall down and alerting the bad guys. They get away and Darkwing tries to show Drakey how to be a super hero.
Lamont shows up and Drakey tries some of his new moves on him and Lamont acts scared and asks Drakey to join their gang. Drakey refuses and Lamont tells him if he changes his mind that they will be robbing a record company. Darkwing plans on going to the record company to stop them but it is actually a trap.
Darkwing and Gosalyn climb up and are ambushed by the bad guys. The bad guys stick musical instruments on their heads. Drakey tries to think what to do when Darkwing drops his gas gun. Drakey puts bubble gum in it and fires it at the trap and stops it. Darkwing and Gosalyn get away and they take on the bad guys. Drakey dons a costume and swings down at the bad guys and grabs the King's wig. The King takes off after him and Darkwing stops him. The bad guys are hauled off to jail and Drakey takes up the idea of being Darkwing.
- When DW returned to his own time, only S.H.U.S.H. was shown reverted back, so we don't know if the rest of the world also reverted back.
- Even if Duckwing didn't shown up and tried to stop the robbery, how come the timeline change before Duckwing appear.
The animation of Darkwing saying, "You're working undercover, right?" was used in Toon Disney's logo in some of the network's bumpers.
- Darkwing: Now wait there, and don't get into any trouble.
- Gosalyn: Really, what kind of person does he think I am?
- Darkwing: Need I remind you about the time with the floor wax, the peanut butter, and my VCR?
- Gosalyn: That was an accident.
- Darkwing: All a superhero needs is a little courage, confidence, and a clean cape!
- The King: That duck is cruising for a brusing
- Drakey: I am the toddler that naps in the night.
- (After Darkwing plays a guitar, tons of debris fall from the ceiling right on top of Darkwing)
- Darkwing: Um...anybody got a...broom?
- Darkwing: I am the cloud that rains on your hit parade.