Clancy left home in the late 1940s to join the Royal Air Force (RAF) where he travelled all over Europe, including Greece and Egypt where he learned many folk songs.

The other duo, Bobby Clancy and Sharon Collen, appeared on Irish television's Ballad Session in 1965.

According to several newspaper articles on Google News Archives they performed some shows in the United States.

When Tommy Makem left in 1969, Bobby took his place and became a member of the Clancy Brothers for the first time.

Bobby resumed his solo work, releasing a solo album Good Times When Bobby Clancy Sings and appearing live on a compilation album from a 1974 German Folk Festival, both in 1974.

Living in Mattapoisett, Massachusetts in the early 1970s, Bobby made a surprise cameo on his brothers' Brockton, Massachusetts TV special in 1974 where he led the brothers and current fourth member Louis Killen on "Mountain Tay."

Liam Clancy and Louis Killen left the group and remaining brothers Paddy and Tom decided to go on a hiatus.

The Clancy Brothers and Robbie O'Connell, now Paddy, Bobby and Liam performed more frequently than they had in the 1970s and 1980s, appearing on numerous TV shows in America and Ireland, notably Live with Regis and Kathie Lee in 1991, 1993 and 1995, Bob Dylan's The 30th Anniversary Concert Celebration in 1992, and RTÉ's Lifelines in 1994.

He left behind a twin sister, siblings Peg and Liam, his wife, four children, and two grandchildren.