39. World’s Most Expensive Pair of Shoes Ever Worn in a Film – $666,000
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The Wizard of Oz was one of these cult classics that people are still watching and loving, almost 100-years after it first came out. Judy Garland happened to wear these ruby slippers during the film when she played the beloved role of Dorothy. They were put through two auctions, the first in 1998 where they were bought for $165,000. But when they were sold once more at a Christie’s auction in 2000 by an anonymous buyer who purchased the pair for $666,000.
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