Another was a girl he met at a restaurant, at her 16th birthday celebration.

A third was a 24-year-old hairdresser of his, who told prosecutors that Mr. Kelly tried to force her to perform oral sex on him. Court documents said she reported that incident to law enforcement officials within two years of when it occurred and handed over a shirt she was wearing that day, which DNA analysis showed had his semen on it. It was not clear why Mr. Kelly was not charged in connection with this at the time. Mr. Greenberg has said it may have been a consensual encounter.

[Read more about the case here.]

For years, Mr. Kelly, whose real name is Robert Kelly, seemed largely immune to accusations that he sexually abused minors and kept women in a cultlike environment, shielded by a series of nondisclosure agreements. But his behavior came under renewed scrutiny in January after the documentary “Surviving R. Kelly,” which chronicled the allegations against him, aired on Lifetime.

He was arrested in 2002 on child pornography charges stemming from a tape that prosecutors said showed him having sex with and urinating on an underage girl. But in 2008, he was acquitted on all counts after the girl prosecutors said was in the tape refused to testify.

That same girl is now the fourth victim cited by prosecutors. They also have said that they have a different tape of Mr. Kelly and the girl having sex, and Michael Avenatti, the celebrity lawyer who gave the video to law enforcement, has said that it is a recording of a different incident than the earlier tape, which removes any concern about double jeopardy.

Mr. Avenatti said on Monday that he had obtained a second video of Mr. Kelly that showed him having sex with an underage girl. He said he gave the 55-minute-long tape to prosecutors, and that the girl in the video was one of the victims Mr. Kelly had already been charged with abusing. In this tape, he said, Mr. Kelly “refers to the victim having a 14-year-old body part, a vagina.”