Animation Source Forums

Well, we just don't know if Baloo *always* had this lifestyle. We don't know how long he had "Baloo's Air Service", how he got it in the first place, when he bought the Sea Duck, we don't know a single person from his family, etc...
It's really a shame the series did not give us any clue on his past. As far as I know, the only scene that belongs to his past is when he's learning to drive in "On a wing and a bear", but even that one doesn't give us much info. (save from his physical appearance - he clearly was thinner back then...)

I, too, use the comic "F'reeze A Jolly Good Fellow!" as a basis for Karnage's age, though I had imagined him younger than 30 for no particular reason before I read that comic. I believe he's somewhat between 32 and 35, based on Dumptruck's line that implies at least some years after 29.

For the following characters I'm just guessing, it's been a while since I've seen the shows or read the comics, so I'll probably be very wrong and oblivious to some facts now

Baloo I imagine below 30. I can't believe he could live his lifestyle prior to Becky for a long time...

Rebecca is probably below 30 as well. My foggy memory claims to remember that she seems like she just finished university.

Wildcat... probably close to Baloo. It's hard to tell with these animals, you're so right Steet...

I think I'll stop and not further embarrass myself anymore, I have no facts behind this anyway.