Apparently this is the first time she's been on the cover. Not a big deal to me, considering I've read things from Meryl saying that she thinks fashion is sort of lame (I'm paraphrasing). Far more interesting is the fact that Meryl and Anna Wintour probably met. I don't know if they have ever met before, but I've seen The September Issue (love) and I imagine that for a cover like this, Anna would have some connection. Why is this a big deal? Two reasons: one, I thoroughly enjoy both of these women, and two, Meryl basically portrayed Anna in her Oscar-nominated role in The Devil Wears Prada. Wintour wasn't portrayed in a particularly positive light, but they're both professionals, and I've actually read Anna being quoted as saying that the attention DWP brought to the fashion industry was a good thing.
I personally think that Anna got a kick out of Meryl's performance and has no problem with being portrayed as "strong." She told Barbara Walters that she thinks it's actually helpful to people to have someone in control and who is able to make decisions. I tend to quote that to Joe to rationalize my bossiness. Here's the Vogue cover that hits stands on 12/20. Super pretty.