Context

Oh Satan, you always did know how to throw together a phrase.

This quote is taken from Satan's monologue in the first book of John Milton's Paradise Lost.

Satan awakens suddenly in Hell, where he finds himself imprisoned in chains near a fiery lake. Next to him is his "mate" Beelzebub (plot twist, Satan is Australian), with whom he starts discussing their fate and their next course of action.

Where you've heard it

This one's a doozy.

It's not necessarily anarchist—Satan himself is a ruler after all—but it's often quoted to express ambition and desire for power. Satan's opposition to God is more based upon what he believes is a lack of God's right to rule the angels; it's a battle for sovereignty.

Hmm, why does this sound suspiciously like the debate between electoral government and monarchy before and during the Restoration? Wait; does that make Charles the II God? And who is the good guy here? Surely not Satan…right?

Frankly, this quote sounds rather power hungry (and the whole serpent thing was really bad PR), but part of what makes Paradise Lost so enduring is the controversy at its core...which is what happens when an evil incarnate being is your protagonist.

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.

Thinking you're an equal of the almighty Lord of Heaven has got to be the definition of pretentious; so why the low score? Well, claiming that it's better to reign than be reigned on isn't necessarily such a haughty thing to say—it may be more of a political statement than a declaration of cosmic warfare.

You also have to consider that this is a widely cited quote; we're talking Paradise Lost here, so a lot of people are going to know you're not just justifying your penchant for Internet piracy and other heinous crimes.