VMA WTF Wednesday: Macy Gray Sent a Subtle Marketing Message at the 2001 VMAs

Wednesday as in today, WTF as in WTF was Macy Gray THINKING when she showed up to the 2001 VMAs in this (obviously DIY) walking billboard topped with a Strawberry Shortcake-on-shrooms hat?

She looks like a Jo-Ann Fabrics (or Mood, for those of you Project Runway fans out there) threw up all over her, and then she held the whole mess together with industrial-strength paper clips. Oy.

Fortunately Macy — who beat out Christina Aguilera (nominated for “What a Girl Wants”) and Sisqo (long live the “Thong Song”!!!) for Best New Artist at the 2000 VMAslooks like this now (more Michelle Williams than Bootsie Collins). But still. You can’t undo the past.

Watch the WTF fashion moments as they unfurl in unfortunate, amazing real-time at the 2008 VMAs this Sunday, September 7.

Plus:
+ Rose McGowan’s Trashbag Tuesday!
+ Emimen’s Mayhem Monday!