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1.
1. A military-style haircut in which the sides are cut very short, while the top is slightly longer and flat. Top is often faded to the sides to make the 'do more uniform. This haircut is a variation of the "high and tight".
2. A box for holding pills. Duh!
Many soldiers in the U.S.M.C. have "pillbox" haircuts.
by Levi Wonder August 21, 2006
 
2.
1. A silly, energetic, crazy, or eccentric person.
It's like saying: "You crazy!" except it's pillbox.

Steeling spoons, constructing elaborate set ups. You guys are such pillboxes.
by Pretzel23 January 01, 2009
 
3.
n. - A military guardhouse, bunker (normally above ground or dug into a fixed position with 360-degree or nearly 360-degree visibility) or other structure from which observation can take place and, under most circumstances, weapons can be fired as a means of defense or security.

*Loosely (possibly incorrectly, this is opinion-based) associated with the term "pillbox" due to its similarity with typical pill boxes, which are used for storing medication, are often translucent (for visibility), and can be opened at will.
Get down! They've got a God damn pillbox up there!
by SnacksCCM August 20, 2014