During a career of more than 30 years, in which he sold more than 100 million records, pop superstar Prince kept a bevy of high-profile lawyers busy—and occasionally bemused. After his death in April, some of his former counsel spoke about a client who was like no other.

Prince had a complicated relationship with the Internet, which required a lot of legal advice. Michael Elkin, now chair of Winston & Strawn’s copyright, entertainment and digital media practice, says he handled some of the first suits filed in the mid-1990s against websites on behalf of the musician, a fierce copyright defender whose music is hard to find on streaming services or Google Inc.’s YouTube. “Prince was a target for commercial suits,” says Elkin. “He was also frustrated by the proliferation of the Internet.