Flanagan returned to working with Fitzgerald in 1968. In addition to being her pianist, mostly as part of a trio, he was her musical director. Her popularity meant that a lot of touring was required: 40–45 weeks a year, including at least one tour of Europe a year (29 cities there in 1970, for example). During these concerts, Flanagan often played a set as part of his trio, without the singer. Beginning in 1974, he again began to perform and record as a leader: his 1975 trio release, "The Tommy Flanagan Tokyo Recital", was his first as leader since 1960. Prior to these performances, he had felt that his technique was inadequate for a soloist, but he enjoyed the extra exposure of being a leader, so decided to continue. Flanagan ended his role with Fitzgerald in 1978, after he had a heart attack and had become tired of extensive touring. After the heart attack, he stopped smoking, reduced the amount that he drank, and exercised by walking more than he had previously.