Underwood was the first House minority whip from 1900 to 1901. He was then House majority leader between 1911 and 1915. Finally, he was Senate minority leader from 1920 to 1923. He was a candidate for the Democratic vice presidential nomination in 1912 and the Democratic presidential nomination in 1924. He was a "wet" (opponent of prohibition), and was the leader of the anti-Ku Klux Klan forces in the Democratic party in 1924.
Underwood was the grandson of Joseph R. Underwood.
Leader, 1911—1915," in Raymond W Smock and Susan W Hammond, eds. Masters of the House: Congressional Leadership Over Two Centuries (1998) pp 91-118