Chris Brown is set to return to court to face a prosecutor who is asking a judge to revoke the singer's probation.
Investigators say they could not find credible evidence he completed his community labour sentence for his 2009 beating of Rihanna.
A motion filed on Tuesday raises several incidents that prosecutors say demonstrate he has continuing anger management issues.
They cited a fight in January between Brown and fellow R&B star Frank Ocean, and a 2011 outburst in which Brown threw a chair through a window after he was asked about the Rihanna attack on Good Morning America.
The filing represents a dramatic shift in the case against Brown, who was repeatedly praised by the judge overseeing his case for his completion of domestic violence courses and his community service work in his home state of Virginia.
That changed in September, when prosecutors raised concerns about Brown's community service after he logged 701 hours in seven months - an amount that had previously taken him more than two years to achieve.
Los Angeles investigators travelled to Richmond, Virginia, to investigate Brown's service.
"This inquiry provided no credible, competent or verifiable evidence that defendant Brown performed his community labour as presented to this court," Deputy District Attorney Mary Murray wrote.
Brown's attorney Mark Geragos blasted the court filing, saying prosecutor ignored interviews "where sworn peace officers stated unequivocally that Mr Brown was supervised and did all of the community service."
After pleading guilty to the attack on Rihanna, Brown was given permission to serve 180 days of community labour in his home state of Virginia, so long as he performed manual labour.