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Attempting to prove his courage after a joke by Louie and Baloo, Shere Khan vows to travel to Pinnacle Rock in the wasteland unaware that the ruthless baboon Mahra and her sons Ned, Jed, and Fred has returned there and wants a new fur blanket.
One day in the Jungle, Shere Khan catches a fish, but is knocked into the river by an eagle, who takes the fish. An embarrassed Khan emerges from the river and hears laugher, noticeing Baloo, who is scratching his back on a nearby tree. Khan tells Baloo not to tell anyone about what just happened, just before Louie emerges from the tree and says that he'll make sure Baloo won't tell anyone. Khan is then angered to learn that Baloo and Louie betted on his hunt, but leaves after once again telling them not to tell anyone.
Back at the ruins, Louie tells Hati, Bagheera and Kaa about what happened. Whilst Hathi finds the story hilarious, Bagheera tells Louie that he shouldn't make fun of Khan as one day he will grow up and then there would be trouble, to which Baloo replies that they will all grow up. Khan soon arrives and gets mad at Louie for telling the others about his hunt. Louie, in his own defence, tells that he said that he wouldn't let Baloo tell anyone.
After a brief scuffle with Louie, Khan tells the others that he isn't scared of anything in the Jungle, before exiting the ruins. However as he leaves, Khan hears Louie talk of he didn't say he wasn't scared of anything outside the Jungle. After Khan returns, the Cubs talk about the Man Village being dangerous, but when Louie brings up the Wasteland, home to the baboon Mahra, whom Baloo says is in the south until the rainy season. Khan, in a attempt to prove his bravery, declares that he will go to the Wasteland that night, and to prove he was there, he will roar from the top of Pinnacle Rock.
After Khan leaves, Bagheera questions Louie if he is up to something, to which Louie gives a nervous look.
Meanwhile in the Wasteland, Mahra has returned to Pinnacle Rock and finds her three sons Ned, Jed & Fred fighting over an animal skin, which gets torn apart in the process. Mahra breaks up the fight and tells them that the animal skin was hers (which she used as a "blankey", before yelling at them to get her a new one, causing the bats living there to fly off, just as Shere Khan is traveling to the Wasteland.
Back at the ruins, Bagheera and Hathi talk off how Baloo, Louie and Kaa went off after Khan. Bagheera then notices the bats and tells Hathi that it is a sign that Mahra has returned to Pinnacle Rock, before setting off to warn the others with Hathi going after him. Meanwhile, Khan has reached the Wasteland and hears a noise which he dismisses as the wind, before hearing another noise and sees three porcupines, which he scares away. Baloo, Louie and Kaa have also reached the Wasteland, but also get spooked by the porcupines and run off, resulting in Kaa falling into a graveyard filled with animal bones and getting stuck in an antelope skeleton. Baloo crawls into the skeleton to free Kaa, but ends up stuck too. Seeing this, Louie gets an idea.
Khan continues to travel to Pinnacle Rock, but turns around to see a large shadowy figure approaching, causing him to panic and run. The figure falls down and Khan is angered to see that it was actually Baloo, Louie and Kaa in disguise. Just then, Ned, Jed and Fred arrive and surround the trio, with Khan leaving them to their fate, claiming that it serves them right. However, before the baboons can harm the trio, Hathi arrives with Bagheera and knocks them away. Mahra then arrives and tells the Cubs to go, except Baloo, who she wishes to make into her new blankey. Baloo attempts to escape, but trips and gets stuck in a ribcage. Mahra prepares to kill Baloo, but sees a tiger roaring on top of Pinnacle Rock and flees with her sons. The Cubs also run, but soon see that the tiger was Khan.
The next day, Khan questions the others about what they were doing. Though the others are unable to come up with a good answer, Bagheera tells Khan that they had come to warn him about Mahra returning to Pinnacle Rock. The Cubs tell Khan that he is the bravest, though Louie says that Khan was scared a little bit. Annoyed, Khan replies that he isn't afraid of anything. Just then a roar is heard, which makes Khan nervous as it is his mother calling. The Cubs laugh as Khan quickly leaves.
- Charles Adler - Ned
- Pamela Adlon - Baloo
- Jim Cummings - Kaa, Fred, Jed
- Elizabeth Daily - Bagheera
- David L. Lander - Arthur
- Tress MacNeille - Mahra
- Jason Marsden - Prince Louie, Shere Khan
- Michael McKean - Cecil
- Rob Paulsen - Hathi
- This episode features the song, "Take Your Sweet, Sweet Time".