Context

This quote is taken from the philosophical book The Prince, written by Niccolo Machiavelli around 1513. 

Sorry, Will Smith—this is not that kind of prince. Throughout all of The Prince, Machiavelli offers arguments for why rulers should often be ruthless to get power and to make sure they keep it. After talking about this stuff for sixteen chapters, Machiavelli opens Chapter 17 by saying that it's better to be feared than loved—if you can't be both. Now, ideally, people would like you and respect you enough not to cross your path. But if you can only have one of the two, Machiavelli thinks it's way better to be feared; otherwise, people will just do whatever they want and society will fall apart. So go out there and get to fear-mongering.

Where you've heard it

This line is a favorite of people all over the place, especially Type-A personalities who find themselves in positions of power. Take Sonny LoSpecchio from the 1993 movie A Bronx Tale, for example. He'd totally choose being feared over being loved.

Additional Notable References

• This is spoken by the Red Queen in Tim Burton's 2010 Alice in Wonderland.

Pretentious Factor

If you were to drop this quote at a dinner party, would you get an in-unison "awww" or would everyone roll their eyes and never invite you back? Here it is, on a scale of 1-10.

It's unlikely that anyone will call you pretentious for saying this quote. After all, almost everyone has heard it in one way or another. Plus, it sounds pretty hardcore. Just don't go and tell them that it's from Chapter 17 of Niccolo Machiavelli's The Prince, published five years after his death. Then people might raise some eyebrows.