Little was rejected by the United States Marines for being underweight). In 1923, he became a reporter and cartoonist at the syndicate of theNew York Herald Tribune.
Prompted by his mother's illness, he returned to the Tennessean. He began drawing editorial cartoons for the Tennessean in 1934 and drew exclusively after abandoning editing and reporting in 1937. He had been tutored by fellow Pulitzer winner Carey Orr before Orr left for the Chicago Tribune in 1917, but a stronger influence was the work of another winner, Daniel Fitzpatrick of the St. Louis Post-Dispatch. His drawing style resembled Fitzpatrick's and the work of both men was noted for biting content. For his part, Fitzpatrick disliked the resemblance and considered Little an "imitator". Little became one of the most influential and republished cartoonists in America.
In addition to winning the Pulitzer, Little won a National Headliner Award in 1948, a Christopher Award in 1953, and a Medal in 1955 and a Freedoms Foundation in 1956.
Beginning in 1934, Little collaborated with Tom Tims (writer of Popeye) on a single panel comic strip for King Features called Sunflower Street, depicting the lives of rural African-Americans. Though well-intentioned, the strip was cancelled in 1949 for fear that the strip would be viewed as condescending and draw racially based complaints.
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