I love this episode alot. It just reeks of comedy gold.
What makes it so good is its setup. Rebecca wins a sweepstakes and has to mail in her ticket by 8am next morning to claim her prize. However, she can't do it herself, so she has Baloo do it. And this is where the real comedy comes into play.
Figuring Baloo would screw it up, she unwisely listens to her daughter about telling him it's not a big deal, which ironically ends up biting her in the butt. I truly believe had Rebecca made it clear how important this was, Baloo would not have made a big mess of things. Would he have still possibly screwed it up? Maybe, but I don't believe he would have wasted most of the money on food at least.
Anyway, the episode gets really good when Baloo realizes he blew it and badly by having it sent to 18th class. So, not wanting to let Rebecca down, he frantically tries to get it there on time, only to miss it by just a few seconds. The scene where Baloo breaks it to her and she says nonchalantly she has to take back the stuff before crying was friggin hilarious. Even the part where she blames herself was funny too because it sadly was true. Had Rebecca been honest with him, things most likely would have turned out better.
And then the icing on the comedy cake was when they found out they could still get that much money by sending in that stamp to a collector, only to find out it was already taken away by the garbage men after throwing it away. Oh the irony...
Sadly, this episode doesn't come without some issues. One, Rebecca never suspects something is wrong when Baloo acts all frantic and tries to hide what he had done when it was blatantly obvious after the mailman was there.
Two, I personally have a hard time accepting someone wanted to buy a stamp for $100,000. Even with today's inflated prices, it's not believable to be frank. Maybe 10,000 I could accept, but not 100,000. Granted, it did make up for it by having the letter taken away to the dump. XD
Anyway, all and all, a top notch episode. Definitely in the Top 3 of best Talespin episodes.