Kelly has a “dark” and “hidden” side that the public rarely saw during his career, prosecutors said at the opening of his second federal trial.
The R&B singer was found guilty of sex trafficking and racketeering in a New York court last year. He was later sentenced to 30 years in jail.
But on Wednesday, a separate trial on child pornography and obstruction charges began in Chicago.
His lawyer urged the jury not to accept the portrayal of Kelly as “a monster”.
Kelly, whose real name is Robert Sylvester Kelly, faces 13 charges, including creating and receiving child pornography, obstruction of justice and enticing minors into sexual activity.
In 2008, he was also accused of trying to rig a similar trial by bribing and intimidating witnesses.
Prosecutors used their opening statements to tell the jury what to expect over the next four or so weeks, detailing the survivors who will testify and some of what the jury is expected to hear.
That includes hearing from one woman – who prosecutors are calling Jane – who will testify that she appeared in an alleged sex tape with Kelly when she was 13 or 14 and the singer was 31.
According to prosecutors, Kelly made four separate videos with Jane – segments of which will be shown to jurors.
That video was the centre of the 2008 trial, however at the time Kelly and Jane denied it was them in the tape. Neither testified and Kelly was acquitted on all charges.
This trial, happening in his hometown of Chicago, is being seen by many as a repeat of the 2008 trial, when he was facing 14 charges of child pornography.
Two of Kelly’s former employees are also facing charges in this trial. Derrel McDavid, his former business manager, is accused of helping Kelly fix the 2008 trial, and Milton Brown is charged with receiving child pornography.
Both men have pleaded not guilty. McDavid plans to testify in court, his attorney said on Wednesday. (BBC)