Every Halloween, the Internet floods with new photos of celebrities in costume. (We’re especially enjoying Robyn as Robin and Amy Poehler and John Krasinski as Andie and Duckie from Pretty in Pink.) But, over the years, a few famous people have emerged as Halloween all-stars. They always dress up, and their costumes are often awesomely outrageous, impressively elaborate, or both. Last year, we pitted daytime TV hosts against each other to determine who (or, more likely, whose wardrobe department) was creating the most entertaining masquerade. Since it looked like Martha Stewart was the clear victor then, in 2011 we’ve thrown her into competition with pop culture’s reigning Queen of Hallowen: Heidi Klum. Follow along from 2005 to the present as we pick a winner.
2005:
Honestly, neither of these two are that inspiring. While Heidi is some kind of pre-True Blood sexy vampire, Martha is “Jane of the Jungle.” Martha’s idea is slightly more original, but — and this really hurts coming from the queen of all that is homemade — her costume looks disturbingly store-bought (or, at the very least, thrown together). We’ll give Heidi some leeway on going vamp, since 2005 was a few years before bloodsuckers went mainstream. Also, her wig is better.
Winner: Heidi
2006:
This is really no contest: It sure is funny to see Martha crawling on all fours, but a half-assed cat costume can never compete with Heidi and husband Seal’s collaborative look. Yes, that’s the man who sang “Kiss from a Rose” in drag as Eve, while Heidi plays the serpent and his fateful apple.
Winner: Heidi (and Seal)
2007:
So, Martha had two costumes for Halloween 2007 — the “Golden Goddess” above (guess the pomegranate means she’s Persephone, even though Demeter might have been more age-appropriate) appeared on the “Good Things” cover of Martha Stewart Living‘s Halloween issue, while a “Glampire” was the face of an alternate “Bad Things” cover. We’ll admit the vampire schtick is overdone, a goddess is still more creative than a black cat (who also appears to be — sigh — a vampire), and no amount of stretch velvet is going to change the way we feel about the matter.
Winner: Martha
2008:
Heidi and Martha both went as mythical goddesses in 2008. But while Martha’s Medusa headdress was really the only great thing about her costume, Heidi went all out as the multi-armed Goddess Kali — the most badass of all the Hindu deities. Yes, that is a belt of human hands around her waist.
Winner: Heidi
2009:
Okay, ladies — the synchronicity is starting to get spooky. Both Heidi and Martha’s 2009 costumes harkened back to classic American literature. Heidi is the Raven, of Edgar Allan Poe fame, and Martha is a “Ghostly Equestrian” (so, basically the Headless Horseman). We think Heidi’s costume is well done, as usual, but only one of these ladies enlisted a real, live horse as a prop.
Winner: Martha
2010:
Oh, we like Heidi’s robot costume all right. And we’ll admit that the concept of Martha’s “Spellbinding Sorceress” is fairly unclear at first glance. But we stand by our praise from last year, in which we decided Martha looked like a cross between David Bowie in Labyrinth and the drag queen Hedda Lettuce.
Winner: Martha
2011:
Heidi had two costumes this year because she threw parties in both Las Vegas and New York, like you do. Apparently, she was both “The Invisible Woman” and “The Missing Link.” So, while Martha looked cute in her punning, Alexander McQueen-embellished “Motha” costume, we’re giving this one to Heidi.
Winner: Heidi
Final score: Heidi – 4; Martha – 3
[All Martha images via MarthaStewart.com]