Mad Hatters: Which Celebrity Wore The Most Ridiculous Hat?

  • Pharrell Williams Hat

    attends the 56th GRAMMY Awards at Staples Center on January 26, 2014 in Los Angeles, California.

  • SXSW Paloma Faith

    <> on March 16, 2013 in Austin, Texas.

  • Cher Oscars

    LOS ANGELES – MARCH 23: Singer/Actress Cher attends the 70th Annual Academy Awards on March 23, 1998 at Shrine Auditorium in Los Angeles, California. (Photo by Ron Galella/WireImage)


    UNSPECIFIED – JANUARY 01: Photo of JAMIROQUAI (Photo by Ian Dickson/Redferns)

  • Lil Kim

    Lil’ Kim (Photo by Jim Smeal/WireImage)

  • Pet Shop Boys Olympics

    LONDON, ENGLAND – AUGUST 12: Neil Tennant of The Pet Shop Boys perform during the Closing Ceremony on Day 16 of the London 2012 Olympic Games at Olympic Stadium on August 12, 2012 in London, England. (Photo by Scott Heavey/Getty Images)

  • TLC Left Eye

  • Bjork Big Day Out Auckland

  • Bill Murray Golf

  • Princess Beatrice Royal Wedding

  • 2013 MTV Movie Awards Hanna Mae Lee

  • Sarah Jessica Parker Hat

  • 2010 MTV Video Music Awards Lady Gaga

  • 2011 MTV Video Music Awards Katy Perry

  • French Montana Bear Hat

  • Jay-Z Obama Inaguration

  • Bruce Willis Demi Moore and Ashton Kutcher

  • BMI Urban Awards T-Pain

  • Pamela Anderson VMAs 1998

  • Erykah Badu MET Gala

A hat, generally is a bold statement. Anything other than a baseball cap and you’re really saying something with your headwear. Iconic hat wearers like Samuel L. Jackson and LL Cool J are simply sporting their signature brand, but what about all the other celebrities who, from time to time, dabble in the hat? Whether in the name of fashion, extreme showmanship or attention getting, celebrity hat wearers have a tendency to skip over “appropriate for the occasion” entirely and just go straight to f-ing ridiculous.

From old classics like Jamiroquai’s menagerie of Cat In The Hat style hats to Erykah Badu’s recent choice for the MET Gala, these crazy celebrity hats will have you wondering whether or not they looked in a mirror before they left the house. With some more endearing than others — like Pharrell Williams now culturally ingratiated Grammys hat — we’ve got some of the most ridiculous hats to ever top a modern celebrity’s head. From the downright abomination of Pamela Anderson’s strange feathered pink UFO-like hat to French Montana’s taxidermic bear, these ridiculous celebrity hats are real head scratchers.

[Photo: Getty Images]