What do Al Capone, Michael Jackson, William S. Burroughs, and Freddy Kruger have in common? Okay, we'll throw in Tom's Wolfe, Landry, and Waits, too. Oh, and then there's Justin Timberlake. Got it now? Dignified and functional, sleek and debonair, the fedora has been a contenda from the gangster days through film noir right up to this year's Ralph Lauren women's wear collection. Did we mention Run DMC? Walk this way!

The fedora first popped up back in an 1882 play by Victorien Sardou, when a heroine named Princess Fedora Romazova first donned the "fedora"-style hat. Typically made of felt, straw, or twill with a pliable rim and lengthwise crease that is pinched on both sides, this distinctive looking topper became an essential part of both formal and business attire in the earlier part of the 20th century. In Britain, the fedora has a shorter brim and is called the trilby. Flatten it out and you have a porkpie. Worn primarily in metropolitan settings to protect against the elements, it was compact enough to fit easily within the confines of expanding technologies such as the automobile. The fedora went on to gain notoriety of a different sort during the Prohibition era when it became the signature style of the mafia. It would also become the fashion of a mobster's foe, the trench coat donning detective.

Thank Hollywood for keeping the hat in the pictures. Humphrey Bogart never went anywhere without one, and Indiana Jones would risk (or at least his outstretched arm) to save his. Rocky Balboa's fedora off-set his ubiquitous leather jacket suddenly turning him into a tough guy with something interesting simmering beneath the surface. So grasp yours properly by its crown, and remember to remove it when in an elevator. Here's looking at you, kid.