One vehicle parked near the jail reportedly played 1996 hit, "I Believe I Can Fly" while a bystander loudly sang along. Kelly was being held after turning himself in to face ten counts of aggravated sexual abuse.
The singer was indicted last Friday in Cook County, Ill. Three of the four victims claim they were underage at the time of the abuse.
Bond was set on Saturday at Sh100 million, and Kelly remained locked up over the weekend.
On Saturday, the court has set R. Kelly's bond at 1 million dollars, with which he has to pay 10% to be out of prison during the trial.
Avenatti, who said he represents two Kelly victims, said his legal team will give prosecutors a second video on Monday that he alleges shows Kelly sexually assaulting a minor. Despite the victim's mother taking away the card and telling the manager that her daughter was only 16, the girl later found the card and the number and was able to call Kelly, who instructed her to skip school and take a cab to his studio, the proffer states.
Kim Foxx - the state's attorney for Cook County, which includes Chicago - told journalists the alleged crimes occurred between 1998 and 2010. Kelly clasped his hands behind his back and was not handcuffed during the five-minute hearing, reports CBS News' Jericka Duncan and Cassandra Gauthier.
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Kelly's lawyer Steven Greenberg insisted the singer was innocent.
Attorney Michael Avenatti says he has another tape to give to prosecutors, but Greenberg isn't anxious.
And on Monday, lawyer Michael Avenatti stated that he is working to obtain new tapes that allegedly show Kelly with underage females. Three of them were under 17 and more than five years younger than Kelly at the time of the incidents.
Last month's release of an explosive docu-series entitled "Surviving R. Kelly" once again brought accusations against him to the fore, however, while a #MuteRKelly movement aimed at preventing his music from airing has gained steam. His lawyer told CNN that Kelly "does not have to pay the child support before getting out".
"The victim also refers to herself as being 14 years of age repeatedly on tape", Avenatti said. He did not say if it was the same 14-year-old girl who he alleged was in the first video he turned over to the authorities. Kelly has consistently denied any sexual misconduct. "We're going to see what the evidence is, and we're not going to worry about some grandstanding".
"I can confirm that we will be providing a second video showing R. Kelly engaged in sexual assault of a minor to prosecutors this morning", Avenatti said in a tweet Monday morning.