Bob Flanigan was born in Greencastle, Indiana in 1926. Following a stint in the military, he enrolled in Indiana's Butler University where his cousins, Don and Ross Barbour, were performing in a barbershop quartet. The group's tenor, Marvin Pruitt, developed stage fright which opened the door for Flanigan in 1948. They changed their name to The Four Freshmen and Flanigan quickly became the group's heart and soul. Unlike other close harmony groups, the Four Freshmen provided their own instrumentation. Known for his smooth trombone playing as much as for his voice, Flanigan played in the style of Stan Kenton and sang in the way he played. (Flanigan also played a stand-up bass viola with the group.)
The Four Freshmen, meanwhile, continue on with a new lineup. The sound that was once favored in jazz circles continues to draw praise from that corner, winning the Down Beat Reader's Poll in 2000 as Best Vocal Group of the Year. They even managed another Christmas album, "Snowfall", in 2007.