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Squall_Line
Non-Fungible Trixie -
My Little Pony - 1992 Edition
The End wasn't The End - Found a new home after the great exodus of 2012

horse butts 🐴
@megaman295  
Well one of the writers mentioned they wanted him to guest star a looong time ago, I think during Season Two, but it didn’t actually happen until Season Four, so the hype train’s been chugging along for quite a while now.
ze
The End wasn't The End - Found a new home after the great exodus of 2012

“Dear Princess Celestia,  
Everything you know is wrong, just forget the words and sing along. All you need to know is that everything you know is wrong.  
Your faithful student,  
Twilight Sparkle”
Spindizzy

Red Miles, now that you mention it, I do remember hear that rumor floating around. It really would be fantastic to have Weird Al on the show, but I wonder if his talent would be best served by a brief cameo role, or a “guest pony of the week” sort of performance.
 
If his pony (or other creature) was a major fixture of an episode, I wonder what the Friendship Report would be about.
Red Miles
Non-Fungible Trixie -
The End wasn't The End - Found a new home after the great exodus of 2012

IIRC sometime over the break between S1 and S2 someone asked Weird Al(on twitter I think) if he would do an appearance on the show. He said he would if they ever asked him to.
Background Pony #3D68
I have heard nothing, but how many would believe a “Weird Al will be in Season 3” rumor?