Woodside, Leigh B., lawyer and judge of the Nineteenth Judicial Circuit, was born in Oregon County, Missouri, February 2, 1848, son of Judge J. R. Woodside, who was born in Kentucky and in 1836 removed to Missouri and settled in Scott County. In 1844 the elder Woodside removed to Oregon County, where he lived until his death in 1887. In 1871 he was elected judge of the Fifteenth Judicial Circuit, comprised of the counties of Oregon, Howell, Ozark, Douglas and Shannon, and was re-elected at the expiration of his term, and by successive re-elections occupied the office until his death. Judge Leigh B. Woodside, the son, received his education largely at the old academy at Steelville, in Crawford County, under the direction of Professor W. P. Rennick, and later W. H. Lynch. He attended the academy from 1863 to 1866. Then he commenced the study of law, and in November, 1870, was admitted to the bar. He immediately commenced practice at Salem, Missouri, with success from the start. In 1876 he was elected a member of the Legislature and served one term. In 1892 he was a Democratic presidential elector. January 10, 1897, he was appointed by Governor Stone to fill the vacancy in the Nineteenth Judicial Circuit caused by the election of Judge C. C. Bland to the judgeship of the St. Louis Court of Appeals. In 1898 Judge Woodside was elected to the circuit judgeship, receiving 9,120 votes, the candidate on the Republican ticket receiving 7,409. Judge Woodside was married in 1868 to Miss Martha Howell, of Scott County, Missouri.
Leigh was named by his father, John R. Woodside, for Benjamin Watkins Leigh, a former United States Senator from Richmond, Virginia. John R.'s father, William, highly regarded him and thought it was a fine name to bestow on him.

In the Missouri State Capital in Jefferson City, Missouri, artist Thomas Hart Benton used L.B. Woodside's image as the grandfather in the family in the famous mural scene that is located in the House Lounge. It is not known from the historical record, why his image was used