Street was a journalist with several southern US newspapers in the twenties.

After he moved to New York with the Associated Press in 1933, he was offered a work writing features for the New York American.

In 1936, he wrote his first book, Look Away! A Dixie Notebook, a series of stories about the South. He is probably most known for his series of historical Dabney novels, set in his home region of Jones County, Mississippi. He worked with James Childers on two novels in the series, although only one was published in both writers' names.