Jacklegg, Jacklegged Share definition Flag Jacklegg - A person or a thing that is always screwing up. 1."Dude,you a freakin jacklegg". 2."Your car is broke again? It's a jacklegg". Jacklegg, Jacklegged by Webmaster Ed/Zamona.com March 8, 2005 0 0 Get merch Get the Jacklegg, Jacklegged mug. Buy Now — $32.95 See more merch