Born in Weldon Spring, Missouri, as Heinrich Nicholas Kolop, Cullop batted and threw right-handed, stood 6 feet (1.8 m) tall and weighed 200 pounds (91 kg).

He began his professional career as a pitcher, second baseman and outfielder for the Madison Greys of the Class D South Dakota League in 1920, hitting .341 in 66 games.

Although he was primarily an outfielder, Cullop continued to pitch sporadically through 1927, compiling a 49–50 record in 140 minor league games.

His prodigious hitting led to major league trials with the New York Yankees, Washington Senators, Cleveland Indians, Brooklyn Robins and Cincinnati Reds (1926–1927; 1929–1931).

He won two regular-season pennants and three playoff championships in leagues ranging from Class C to Triple-A before he retired from managing in 1959.