Meader began his career as a musician but later found fame in the early 1960s after the release of the 1962 comedy record "The First Family", written and produced by Bob Booker and Earle Doud. The album spoofed President John F. Kennedy – who was played by Meader – and became the fastest selling "pre-Beatles" album in history and went on to win the Grammy Award for Album of the Year in 1963. At the peak of his popularity, he performed his Kennedy impersonation on variety shows and in nightclubs around the country and was profiled in several magazines.