Bitters are extracts of various culinary components that get soaked in neutral alcohol, bringing a dash of complexity to mixed drinks like the old fashioned. Out of all the brands, Angostura bitters is arguably the most recognizable with its oversized label — although many don’t know how this design came to be.

Angostura bitters were created in 1824 by Dr. Johann Siegert, and his sons took over the family business in the latter half of the 1800s. In this period, Angostura bitters started winning awards at various expositions, and the Siegert brothers decided to divvy responsibilities for one competition — one would design a new bottle while another would create the label.

Unfortunately, the two brothers did not communicate while making their designs, which resulted in a label that was too big for its bottle. Although the mismatched design did not win, it earned praise from one of the judges for its memorable look, and the brothers chose to make this accident permanent.