Falling in Love with Jazz was released in 1989, continuing Rollins' prolific period on the Milestone label. The album was again produced by Sonny and Lucille Rollins, and featured prominent musicians such as guitarist Jim Hall and pianist Tommy Flanagan. The recording reflects a more relaxed and lyrical approach, contrasting with some of his earlier, more energetic works. Critics praised the group's cohesion and the maturity of the performances.
The album's sound is predominantly acoustic, with an emphasis on smooth melodies and elegant arrangements. Songs like 'Falling in Love with Love' and 'For All We Know' showcase Rollins' ability to approach ballads with unique emotional depth. The interaction between Rollins and Jim Hall is particularly notable, creating musical dialogues full of subtlety.
The legacy of Falling in Love with Jazz is that of an album celebrating the love for the genre from a mature perspective. It is considered an intimate and reflective work, demonstrating that Rollins could be as compelling on slow tunes as on fast ones. Over time, it has become a favorite among followers who appreciate his more romantic side.