Telly and Oscar

Even I can remember a time when Telly considered Oscar to be his best friend before he and Baby Bear were... if fact, I think their friendship lasted into the waning days of the old-school era, and into the earlier part of the ATC era.

But since this too was a little before my time, I have to wonder, how exactly did Telly and Oscar come to be "best friends"? I mean I'm curious as to why Telly willingly tried to hang out with someone like Oscar in the first place, and why he considered him his best friend, even though at times, he treated him like crap (ala Big Bird in China where Telly wishes to go to China, so Oscar makes him dig their way there, then when they get there, Oscar is unimpressed and decides they should go home, after Telly spent all that time digging). Also, when exactly did their friendship begin? I'm assuming it was fairly early on, considering some of their interplay dates back to when Brian Meehl still played Telly.

I think it's one of those things that just clicked really well. They probably did a Telly and Oscar storyline and realized it was a fun combination. I always knew they worked well together. Yes, around 93, or 94 Telly's obsessive behavior towards Oscar toned down a bit as he was paired with Baby Bear. I do however miss the old days when he worshiped Oscar as if he was some sort of hero. Telly saw something in Oscar that nobody else ever saw, and Oscar loved this because it made it easier for him to to play mean tricks on Telly and give him a hard time. I often wonder if the writers phased this out because it would send across a message to kids that it's okay to let someone bully you if you think theyr'e "cool"

That's actually an interesting take.

Marty explains the reason in his Muppet Mindset interview. Telly's evolved so much since then, saying he's kinda immune to Oscar now.