Transcript for 'George Michael: Freedom' doc offers rare glimpse into singer's life
Reporter: One of the most iconic songs of the '90s. ??? Freedom ??? You're striving to make something every time you're in the studio half as good as a record like that. It's the Mona Lisa. Reporter: It was actually the music video for "Freedom 90" that marked a career highlight for George Michael. George pitched it to me in L.A. In a nightclub called Roxbury's. "You're the leader of the gang, unless you say yes, the rest of the girls won't." Reporter: The story of how five supermodels came to lip synch the hit told in the documentary "George Michael: Freedom." You look like you're singing it, can you act like you're singing along to it? When I had just learned it. Oh my god, let's just have fun, and that's what it ended up being, fun. Reporter: Chock full of interviews with celebrities who knew and loved him. He's god's gift to the world. Reporter: The film covers his life and career, made before his untimely death from natural causes last Christmas at age 53. I'm aware of the need for persona. And my actual persona, I'm not really prepared to give. Reporter: The notoriously private star codirected with his lifelong friend and songwriter David Austin. Would he have been promoting this movie? No. He made the film, narrated the film, that's about as far as he got. He was one person that he just -- you know, he just didn't -- celebrity wasn't for him. Reporter: The project was intended to be released alongside the 25-year anniversary reissue of George's second solo album "Listen without prejudice" which he refused to remote. The track "Freedom 90" from that album a symbolic line in the sand for George. With the burning of his jacket and the significance of it. It had a lot to say. I got the impression, that chapter's closed, I'm done, I'm done being a public figure pop star, I just want to make music. ??? Reporter: His exit from the limelight would lead to a highly publicized battle with record label Sony. George Michael is today asking a high court judge to declare his recording contract null and void. I think he was very honest about his court case with Sony, which he had never spoken about before. There's a massive reveal it in, he says he wished he'd never done it, wished he'd never gone to court with Sony in the first place. I will never know if Sony and I would have ended up in court had Anselmo not become ill. Reporter: Anselmo Felipe pa, one of George's few true loves. Learning months into their relationship that he was HIV positive. In front of his 160,000 people, there was this guy over on the right-hand side of the stage that fixed me with this look. It was so cute. I was so distracted by him. I stayed away from that end of the stage for a while. The moment I looked at him, I got a feeling that told me I was going to know him very well and that he was going to be a part of my life. ??? Somebody to ??? Reporter: His 1992 performance of queen's "Somebody to love" sung to honor lead singer Freddy Mercury, who died from aids-related complications, also a tribute to Anselmo. Anselmo was the first time I think I really loved someone selflessly. Reporter: Anselmo passed away the following year, 1993. And George's beloved mother would follow in 1997. How important was his pain to his success? He says in the film that, you know, back in the day, the grief that he felt having lost his mother and having lost his partner I think he felt that he would -- like for example, older was an album that followed "Listen without prejudice." He openly says that without having felt that kind of pain, he would never have been able to have made an album like "Older." ??? Don't you think I'm looking older ??? Reporter: The showtime documentary looks at the questions of race and music raised by George's work after his debut album "Faith" -- George -- Michael! Reporter: Won in soul and r&b categories at the American music awards. I've been a lover of soul music since I was a kid. He picked up these two awards in categories that were traditionally for black artists. And the problem with our industry, they do love to pigeonhole people. He uniquely achieved breaking into the r&b/soul charts that few white performers ever got. I think there was an attempt to kind of steal black heritage in what I'm doing, all that's happening is I'm trying to make good music. Reporter: That iconic album will be reissued today. For a new generation of fans, his enduring legacy. In a rare interview with ABC news in 2008, George Michael shared his view that fame and beauty are fleeting, keenly aware his time here would someday end. I don't inhale any of that -- it dangerous. What I really am is a writer. And, you know -- I never thought looks are much to begin with, they'll fade. My brain will go. Eventually it's all gone but the songs are still there. Reporter: Songs like his classic ballad "Father figure." ??? Iill be the one who loves you ??? ??? till the end of time ??? Reporter: For "Nightline," I'm T.J. Holmes in New York. George Michael "Freedom" premieres on showtime this Saturday.
This transcript has been automatically generated and may not be 100% accurate.