- He was brought in as the defense's lead attorney in the renowned "Scopes Monkey Trial" in Tennessee in 1925, and as such was the basis of the character Henry Drummond in the play and various film and TV versions of Inherit the Wind (1960).
- His hobby was doing crossword puzzles, which grew into a near-obsession. Once he was so intent on finishing a crossword puzzle while on his way to court, he had a policeman lead him by the arm so he wouldn't have to take his eyes off the puzzle.
- America's most famous defense attorney in the early 20th century, known for representing murderers (including Nathan Leopold and Richard Loeb), Communists and anarchists.
- He was the basis for the character Jonathan Wilk in the book and film Compulsion (1959), which was based on the Nathan Leopold-Richard Loeb case.
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