Roosevelt, the grandson of President Theodore Roosevelt's first cousin, James West Roosevelt was the son of Oliver W. and Verdery Akin Roosevelt of Long Island, New York. He attended schools in Long Island and the Asheville School in North Carolina. He went on to study music at Harvard University, where he was a member of the Harvard Glee Club and a pupil of composer Walter Piston. From 1946 to 1947 he served in the U.S. Navy, and in 1948 he became program director for WQXR, a New York City classical station. Two years later he accepted the position of manager for the Birmingham Civic Symphony.
In 1954, Roosevelt became an editor for the Shades Valley Sun. In 1960 he joined the News as a music critic and radio/television reporter. In addition to reviewing more than 3,000 concerts, he served as an advisor to numerous local arts groups. He also taught music appreciation courses at UAB and Birmingham-Southern College.
He continued his involvement in the music community, serving on the boards of the Alabama Symphony Orchestra's Volunteer Council, the Birmingham Chamber Music Society, and the Red Mountain Chamber Orchestra. In 1985 he organized the massive Basically Bach Festival celebrating the 300th anniversary of J. S. Bach's birth. He also assembled a 1000-piece choir and orchestra to perform W. A. Mozart's Requiem in 1991, the 200th anniversary of that composer's death.
Roosevelt retired from the News in 1991. He died in 2007 after a long illness. He was survived by his wife, Ann, and five children, Verdery, Oliver III, Laura, Mary and Carolyn. A memorial service was held at St Luke's Church in Mountain Brook. He is buried in Cartersville, Georgia.
- Roosevelt, Oliver (n. d.) Music is My Mistress. unpublished memoir.
- Huebner, Michael (January 10, 2007) "Oliver Roosevelt, classical music critic at The News from 1960-1991, dies at 79." Birmingham News.
- Nelson, James R. (February 11, 2007) "Memorable Roosevelt legacy spans visual and performing arts." Birmingham News.