Montgomery graduated from Germantown Friends School in 1945, and he earned his bachelor's degree in painting and music composition in 1950 from Bethany College in Lindsborg, Kansas.
[3] In 1951, he was drafted and sent to Korea to serve in the 45th Infantry Division of the United States Army during the Korean War.
[2] Also in 1956, Montgomery took over as director of the Penn Glee Club and served in that position for 44 years until his retirement in 2000, writing, directing, choreographing and conducting their shows, and bringing the glee club on tours to 30 countries on five continents.
[4] For the Glee Club, Montgomery composed the "Academic Festive Anthem", using words by Benjamin Franklin.
[5] He also helped to create the Penn Singers as a light opera and musical theatre company in 1971 and continued to serve as their director until his death.
[6] After his 1963 "Irish folk opera" Spindrift, was performed by the Penn Players,[7] he wrote the music and lyrics for a 1964 off-Broadway show, The Amorous Flea with a book by Jerry Devine, based on Molière's L'École des femmes (The School for Wives)[8] is still performed occasionally.
[10] From 2000 until 2008, he sold his original notecards, featuring his watercolor artwork, through his company, Monty, Inc.[11] In 2005, Montgomery received an honorary doctorate from his alma mater, Bethany College.
[6] Montgomery, a resident of Chestnut Hill, Philadelphia, Pennsylvania, died of heart failure at his summer home on Spruce Head Island, Maine, the day after his 81st birthday.
[2] On October 5, 2008, a memorial service was held for Montgomery in the Irvine Auditorium on the University of Pennsylvania campus, where he conducted many concerts.