Since his debut in 2005, Chris Brown has been a mainstay in the music industry, for some good and a lot of bad. Heralded for his vocal skills and dancing talent, his star power was virtually undeniable from as early as 16 years old; in the beginning of his career, he released two top five albums and five top 15 songs in the span of two years.

By 2009, though, Brown had become a pariah, shamed after a heartbreaking and horrifying assault on Rihanna. He began lashing out in public and on social media, earning a reputation for both assholerly and outbursts. While he retained an active fan base, his overall social standing in the hierarchy of pop culture began to fade. As a result, the Virginia native lost a lost of good will and a lot of good advertising deals.

He’s never had an album debut lower than number seven on Billboard’s charts, but later in his career, his personal life and actions have clouded and overshadowed his sales. From his relationship with Karrueche Tran, to a standoff with Los Angeles police, to being arrested in Florida earlier this year, turmoil has followed him throughout his career, the good majority of it invited by his own actions.

Chris Brown’s various dramas, which have played out over a series of 13 years, are detailed below.