Chris Brown

Chris Brown earned his first No. 1 on the Billboard Hot 100 chart with his 2005 single “Run It!” His self-titled album was released later that year, winning BET Award for Best New Artist in 2006. Following hit singles “Kiss Kiss,” “Run It!” and more, Brown’s 2011 album, F.A.M.E., earned him a Grammy Award for Best R&B Album.

Brown made his acting debut on season 4 of The O.C. and starred alongside Ne-Yo and Meagan Good in 2007’s Stomp the Yard.

In 2009, Brown faced domestic violence charges after an argument with his then-girlfriend, Rhianna. He pleaded guilty and received five years of probation and six months of community service at the time and was ordered to attend domestic violence counseling.

Brown went on to date Karrueche Tran before briefly reconciling with Rihanna in 2013. He shares daughter Royalty with Nia Guzman and son Aeko with Ammika Harris. Brown was later linked to Diamond Brown, with whom he shares daughter Lovely.