The Bolo (or Bolas) Arrow
No doubt about it, it's a classic. Along with the Boxing Glove Arrow, it's one of the trick arrows featured in Kevin Smith's revival of Green Arrow back on 2001.
Always a crowd-pleaser. And it's been a staple of G.A.'s quiver for quite some time. But just how long has it been around?
Well, it seems to have debuted in More Fun Comics #77.
Which makes it not only a very old trick arrow, but, as near as I can tell, the FIRST trick arrow. Prior to this, Green Arrow and Speedy just do arrow-tricks. The closest thing to a trick arrow is just tying a rope to an arrow. Which is cool, but not as "fantastic" as an arrow that releases a bolas to ensnare a fleeing suspect.
I submit the above panel is the first use of a trick arrow ladies and gents! Bask in its glory. :)