"I think a lot of us kind of tolerated or looked the other way on that issue for a long time," Legend said on the morning show about how stories of Kelly's sexual misconduct have been around the industry for years.
"Let justice play out," the singer continued when asked what he thinks should happen to Kelly. "His victims deserve justice."
Legend previously spoke out against Kelly in Lifetime's Surviving R. Kelly which chronicled the sexual assault allegations.
Kelly was released from Cook County Jail on Monday after posting bail. He has been charged with 10 counts of aggravated criminal sexual abuse against four people, three of which were under the age of 17 when the incidents took place.
Kelly entered the pleas of not guilty on all 10 counts. He is scheduled to return to court on March 22.
"We dated in the same circles," Legend said to host Seth Meyers. "We would hang out at like Sports Illustrated: Swimsuit Edition parties and things."