The general political outlook in Italy was of the gloomiest, and the country was on the eve of the catastrophe of foreign invasion.
The unsparing satirist described the professor's face as the "gloomiest" in the whole procession of ecclesiastics which took place on Good Friday.
In 1779, at almost the gloomiest stage of the war in the southern states, Jefferson succeeded Patrick Henry as the governor of Virginia, being the second to hold that office after the organization of the state government.
How would you define gloomiest? Add your definition here.