Hassall's father, who had served in the fleet at the siege of Sevastapol, was paralysed as the result of an accident on board ship.

After twice failing entry to The Royal Military Academy Sandhurst, he emigrated to Manitoba in Canada in 1888 to begin farming with his brother Owen.

At the suggestion of Dudley Hardy (along with Cecil Aldin, a lifelong friend), Hassall studied art in Antwerp under Charles Van Havermaet and Paris.

[2] In 1895 Hassall began work as an advertising artist for David Allen & Sons, a career which lasted fifty years and included such well-known projects as the poster "Skegness Is so Bracing" (1908).

Hassall's design was continually updated to reflect changing fashions and trends and was longer-lasting and of greater international significance than his Jolly Fisherman.