(CNN) — Here is a look at the life of Grammy Award-winner Chris Brown, who pleaded guilty to assaulting then-girlfriend Rihanna in 2009.

Children: with Nia Guzman: Royalty; with Ammika Harris: Aeko

Has been nominated for 26 Grammy Awards and won two.

November 29, 2005 – Jive Records releases Brown’s debut album “Chris Brown.” It peaks at number two on the Billboard 200 chart.

2007 – Film debut in “Stomp the Yard.” He also appears in three episodes of the television series “The O.C.”

December 2008 – Billboard names him “Artist of the Year.”

February 8, 2009 – On the eve of the Grammy Awards, Brown assaults girlfriend Rihanna (Robyn Rihanna Fenty) inside a rented Lamborghini on a Hollywood street, leaving her face bruised and bloody. He is arrested and later released on $50,000 bail.

April 6, 2009 – Pleads not guilty to felony charges of assault and making threats related to the February domestic violence case.

May 27, 2009 – A photographer files a lawsuit against Brown, claiming Brown’s bodyguards roughed him up outside a fitness center when he took a photo of the singer. The lawsuit is settled in 2010.

June 22, 2009 – Enters a guilty plea to one felony count of assault with the intent of doing great bodily injury in connection to the February assault. He is later sentenced to five years’ probation, and must serve 180 days (about 1,400 hours) in labor-oriented service, and undergo a year-long domestic-violence counseling class.