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Simon was born and died in New York City, New York. Simon was born into a wealthy and talented family. Not only was his father wealthy, but his brother, Richard L. Simon, was the co-founder of the American publishing house Simon & Schuster, and the singer-songwriter Carly Simon is one of his nieces. He graduated with a BA from Harvard University in 1934, and began working for the music magazine Metronome the following year. He became editor-in-chief of Metronome from 1939 to 1955and shifted it, from writing technical articles, to being a chronicler of the swing era. Simon was probably the most influential jazz commentator during the swing era. Thanks to his inside connections with the jazz world, he was able to report information about bands and their personnel with great accuracy. After leaving Metronome, he was involved with the Jazztone Society (1956-57), was a consultant for the Timex Jazz Shows, and wrote about jazz for the New York Herald Tribune and the New York Post newspapers. He also did liner notes for a variety of musicians, including Thelonious Monk who was stylistically quite different from the swing-era musicians Simon championed. In 1978, he won a Grammy Award for Best Album Notes.

He died of pneumonia in 2001, after years of suffering from Parkinson's disease. He was inducted into the Big Band and Jazz Hall of Fame the following year (2002).

The Sinatra Report 1965

The Big Bands 1968

Glenn Miller and His Orchestra 1974

The Best of the Music Makers 1979