Alan J. Stein, a prominent entertainment lawyer, passed away on Dec. 6 in New York City. He was 89.

Over the course of Mr. Stein's 50-year career he worked as a senior partner in the firm of Zissu, Stein, Bergman, Coutre & Mosher as well as Stein and Stein.

His impressive roster of music clients included Lou Reed, The B-52s, Bachman Turner Overdrive, Loverboy, Sire Records and Sire co-founder Seymour Stein, and record producers Bob Rock and Bruce Fairbairn. He also counseled legendary non-rock clients such as classic American songwriters and producers Leiber & Stoller and the Tommy Dorsey Orchestra.

Seymour Stein said in a statement, "Alan Stein, no relation in reality, was like a big brother to [Sire co-founder] Richard [Gottehrer] and I, and he helped us set up the legal side of Sire Records. He was far more than a lawyer for us. His career went all the way back to the big band era and he also represented a lot of talent out of Canada, including Bryan Adams at one point. His knowledge of the publishing side of the business was amazing."