As Mr Cosby walked toward court, accompanied by two publicists and a police escort, Nicolle Rochelle climbed over a barrier and began shouting.
In addition, at the prior trial, prosecutors called up to the stand one woman who said Cosby had previously drugged and assaulted her, as prosecutors attempted to show that Cosby had a pattern of misconduct.
The pioneering black entertainer's first trial ended in a hung jury in June previous year, with a sequestered panel hopelessly deadlocked after six days of testimony and 52 hours of deliberations.
In an interview after her arrest on disorderly conduct charges, Rochelle said she is a performing artist and activist who now lives in Paris.
Cosby's lawyers produced documents referencing the criminal past of another, Chelan Lasha.
The accuser in the case, Andrea Constand, 44, is one of more than 50 women who have accused him of sexual assaults, some dating back decades. Last time, Mr Cosby had jurors brought in from Pittsburgh, 480 kilometres away, because he was concerned locals would be affected by the pre-trial publicity.
The defense will deliver its opening statement Tuesday in a trial expected to last a month. She will tell you that she did not say "Yes". She said that nothing inappropriate had happened on the set with Cosby, whom she said she liked as a young actress.
She also had on her body the first names of some of Cosby's alleged victims, including Andrea Constand, whom the 80-year-old funnyman is accused of drugging and molesting in 2004.
The settlement amount had been confidential - and was kept out of the first trial - but a judge ruled that both sides could discuss it at this one.
About a dozen other protesters also demonstrated outside the courthouse.
"In honor of the first day of the Bill Cosby retrial, I went by the address where they filmed The Cosby Show exterior in New York City.LET'S HOPE JUSTICE WILL FINALLY BE SERVED!" she captioned the photo.
The phrase reportedly refers to something his late son Ennis Cosby used to say.
Also known as Nicole Leach, she was quickly detained and placed into local police custody, but not before creating a surprising and chaotic scene as Cosby's sexual assault trial gets underway once again.
Nicolle Rochelle, the woman who executed a memorable protest at Bill Cosby's retrial on Monday, has a past history with the fallen actor-but it's not what you may think. This time out, Cosby has hired more of an outsider to lead his defense: Thomas A. Mesereau Jr., a high-profile criminal defense veteran who helped Michael Jackson win acquittal in his 2005 child molesting trial.
In a 2005 deposition, Cosby said he gave Constand an over-the-counter antihistamine to relieve stress and that they had consensual relations, but admitted obtaining sedatives with a view to having sex.