"Plunder and Lightning" when Rebecca sings a lullaby to Molly and notices Kit Cloudkicker is wistfully watching her as a mother he will never have. Although he tries to hide, Rebecca finishes her song by leaving out the cookie jar for him to take a cookie to show silently that she cares for him too. (This scene is unfortunately cut from reruns and even the DVD, but you can watch it on YouTube.)
The end of "The Old Man and the Sea Duck", when Baloo realizes the gift that the ghost of Joe McGee has given him. "Look around you, Baloo. The skies are yours..." Can also double as a Tearjerker.
The entire premise of "A Jolly Molly Christmas" revolves around Baloo and the others' extreme attempts to maintain Molly's faith in Santa Claus and somehow make her Christmas wish come true (for it to snow just as her mother desires). After it seemingly falls apart and Molly runs off heartbroken and disillusioned, the crew reunite with her, just as the first snowflake falls from the sky.
Not to mention the ambigious nature as to just why and how the snow falls. The scene plays out in a very strange way, and all Molly says afterwards is "Mommy, I saw him!" When Louie asks Baloo who she means, Baloo replies "Louie, you wouldn't believe me if I told you." The answer is left up to the viewer: was it Santa Claus? Or was it.....
Mixed somewhere between this trope and a Moment Of Awesome, "My Fair Baloo" involves Baloo embarrassing Rebecca with his oafishness at a Business Man's ball. After saving her and the other guests from an armed robbery and plane crash, he is still thrown out by the other members. A furious Rebecca chews them out, realising wealth and eloquence don't make a benevolent person and storms off to find Baloo. While the ball is hijacked by the same armed robbers ("small world, ain't it?") Rebecca is attacked by a giant snake, which Baloo instantly rushes out and saves her from.
Rebecca: Wake up, you weasels! That man just saved our lives. Maybe he's crude and 'rough around the edges', but I'd take him over all of you put together!
There are so many heartwarming scenes in the 2 part episode "A Bad Reflection on You", most notably when Kit brings Baloo out of his BSOD,
Baloo: Stop it, you hear me? Just knock it off! I'm a loser, a failure. I crashed my plane, I lost my cargo, and thanks to me a very big boat's gonna get sunk and I can't cut it I tell ya! Just, just leave me alone.
Kit: Papa Bear?
Kit: I still think you're the best.
And the scene where Baloo stands up for Kit as they're escaping from the air pirates.
Wily: This boy's enthusiasm is gonna get us all killed!
Baloo: This boy happens to be Kit Cloudkicker! The best navigator in these skies, and we're a team see? So if he thinks we can do it, we can do it! (to Kit) So? Do it!
The scene in "Sheepskin Deep" where Rebecca learns that Baloo has been secretly studying to earn his grade school degree—during his deliveries—throughout the episode. Baloo thinks that Becky will be angry, but instead she congratulates him on trying to better himself and tells him to take the day off and continue studying.
Baloo and Kit's reconciliation at the end of "Stormy Weather".