The only scenario I can imagine Taylor Swift getting a Tony or Oscar (especially a Tony) is as a songwriter/composer. I mean acting? Forget about it. Singing? Nah. Both at the same time (probably in the case of a Tony)? Absolutely not. She's more likely to get an Oscar, if that makes sense. Writing separate 4 minute tracks on an album is not the same as writing a coherent storyline complete with character development with music. I mean Cyndi Lauper managed it, but that's Cyndi Lauper.