'The September Issue' Rewatch: Anna Wintour, Grace Coddington, and the Sienna Miller Hair Crisis (with Kate Casey)

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The September Issue is R.J. Cutler's 2009 documentary about the biggest issue of Vogue ever made up to that point — 843 pages, 13 million copies sold.

Amy is joined by Kate Casey, host of Reality Life with Kate Casey and a documentary and reality TV expert, to rewatch it seventeen years later. They get into what Anna Wintour really thought of the film, why she and her Vogue team hated Sienna Miller's hair so much, how it all aged, and much more.

CHAPTERS

00:00 Introduction

02:00 13 million copies sold — and what's left now

06:00 How Anna and Grace actually met

17:30 The retailers' breakfast, when Vogue set the trends

25:00 "Your girls always look the same" - Anna at her harshest

41:00 Anna at home, and the kids who didn't follow her

48:00 The Sienna Miller cover disaster

1:07:00 843 pages, and the era that ended