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Jennings is an alumnus of St. Olaf College and sang as a member of the St. Olaf Choir as an undergraduate. He received his master's degree from Oberlin College and his doctorate from the University of Illinois. Jennings was appointed to the faculty of St. Olaf College in 1953, and ascended to one of the world's most coveted choral podiums in 1968: Jennings was the third director of the internationally renowned St. Olaf Choir, succeeding founder F. Melius Christiansen and his son-successor, Olaf C. Christiansen. He retired from St. Olaf College in 1990, turning over the podium to his former student, Anton Armstrong. His Son, Dr. Mark Jennings, is the director of Choral Activities at Truman State University in Kirksville, Missouri.
As director of the St. Olaf Choir Jennings became noted for guiding and maturing the St. Olaf Choir from one rooted substantially in its 1911-era founding to arguably one of the most highly respected choral ensembles of the world. While Jennings never forsook the choir's Lutheran heritage, he successfully broadened the ensemble's repertoire to include works of noted composers of the post-World War II era.
He also modified the Christiansen tradition of programming exclusively sacred a cappella music to include works with orchestral and/or instrumental accompaniment. Jennings prepared the choir to record Ravel's [Daphnis and Chloe] with the Minnesota Orchestra under the direction of Stanisław Skrowaczewski, and during his tenure, he arranged for several notable conductors to rehearse and lead the Choir in concert, including Polish composer Krzysztof Penderecki, Bach specialist Helmuth Rilling, British organist Simon Preston, and Robert Shaw. Jennings led the choir on 12 international tours, most notably to France (where he led the St. Olaf Choir, Strasbourg Philharmonic and International Soloists in Bach's B Minor Mass for the Opening Concert of the 1972 Strasbourg International Music Festival), Norway (for the Bergen International Festival), and to Seoul, Korea (1988 Summer Olympics Arts Festival.
Since his retirement from St. Olaf in 1990, he has served as a visiting professor and choral conductor at Gustavus Adolphus College in St. Peter, Minnesota and The University of Arizona, Tucson. Jennings served as the guest conductor at anniversary concerts in honor of F. Melius Christiansen (the 125th in 1996 and the 135th in 2006).
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