Plans for a memorial service are pending.
Robert Lee Flanigan was born Aug. 22, 1926 in Greencastle, the son of Minter and Nellie Flanigan. The bandshell in Greencastle's Robe-Ann Park was named The Bob Flanigan Bandshell in his honor in June 1991.
He is survived by his wife, Mary; a sister, Maxine Thomas, Greencastle; his children, Scott, Jill, and Stephen Flanigan, Julie Maple, Jennifer Turner and Debbie Muria, and 15 grandchildren.
Flanigan died of congestive heart failure Sunday at his home with family members nearby and eight local trombonists playing songs, IVI Management agent Dina Roth said.
From an early age Flanigan was enthralled with the sound of jazz, especially big-band singer and trombonist Jack Teagarden and bebop saxophonist Charlie Parker.
Upon completing a stint in the military during World War II, where he served in Germany, Flanigan enrolled at Butler University in Indianapolis, where Hal Kratzsch and brothers Don and Ross Barbour had formed a barbershop quartet with Marvin Pruitt.
When Pruitt developed stage fright and decided to quit, it opened the door for the Barbours to reach out to their cousin Flanigan. After he came aboard in 1948, the quartet changed its name from the Toppers to The Four Freshmen. Flanigan, a tenor, played trombone and bass and sang lead parts.
The Four Freshmen perform "Angel Eyes," "Route 66," "Polkadots" and "Moonbeams" live in Japan in 1964. Bob Flanigan is second from the left.
"Flanigan's voice was indestructible," said Ross Barbour, the last remaining original member of the four-man group. "He could drive all day and all night without stopping between gigs, and when our voices were on the edge Bob was still in full form."
Barbour, 82, now lives in Simi Valley, Calif.
Don Barbour died in a car crash in 1961. Kratzsch died in 1970.
The group produced more than 50 albums and 70 singles, and had six Grammy nominations over the years. Best-known recordings were "It's a Blue World" in 1952, "Mood Indigo" in 1954, "Day by Day" in 1955 and "Graduation Day" in 1956.
"Bob Flanigan and The Four Freshmen were my harmonic education," Wilson told the Los Angeles Times through his manager. "I saw them at the Cocoanut Grove in Hollywood in 1958. My dad and I went backstage and met The Freshmen. I was nervous because they were my idols. They were so nice to me. I was just 15 years old. I'll forever miss his friendship."
All members of The Four Freshmen also played instruments, which made them unique among close-harmony vocal groups of the era. In addition, Flanigan's exceptional vocal range allowed him to take the melody above the other three voices, which also opened new vistas in male quartet singing. The Freshmen were inducted into the Vocal Group Hall of Fame in 2001.
Flanigan retired in 1992, but he kept a hand in the changing cast of performers and management of The Four Freshmen name.
Flanigan often credited big band leader Stan Kenton as being the key influence on what The Freshmen wanted to achieve, a sound built on more sophisticated harmonies than typical of the male vocal quartets that preceded them.
A friend of Kenton's urged him to see the group because it had developed a reputation of having a vocal sound like that of his band. He promptly connected The Freshmen with officials at his record label, Capitol, which signed the group and soon released its first hit, "It's a Blue World," in 1952.