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O'Brian was born in Buffalo, New York. He dropped out of elementary school to take a series of menial jobs and eventually landed a position as a cub reporter for the Buffalo Courier-Express. He joined The Associated Press as a drama and movie critic in 1943. In 1949 he moved to the "Journal-American" and started its popular television column. He was known for his lively style and often negative opinions.[citation needed]
O'Brian was pivotal in the exposure of the quiz show scandal centred around the quiz show Twenty-One. In 1958, he published the contention by former contestant Herbert Stempel that the NBC game was rigged. Later came an investigation by New York County Assistant District Attorney Joseph Stone that led to Grand Jury testimony and ultimately Congressional hearings in 1959. The House probe, led by Congressional investigator Richard N. Goodwin, resulted in the dramatic admission by the man who had defeated Herb Stempel on Twenty-One,Charles Van Doren, that the program was indeed fixed.[citation needed]
In the 1970s and 1980s, O'Brian conducted a daily afternoon interview show on WOR Radio in New York, "The Critic's Circle," focused on entertainment.[citation needed]