XXL celebrates 50 years of hip-hop with this moment:

Aug. 16, 2000: Eminem is one of the most successful rappers in hip-hop, but during the height of his career, his marital life with Kimberly Mathers was at the forefront. After years of a rocky relationship, Em filed for divorce from Kim on this day in 2000.

Eminem and Kimberly Mathers met in high school, and were in an on-and-off relationship for 15 years. The couple also raised their only child, Hailie Jade Mathers, together. Em and Kim wed in 1999. Their marital problems became the subject of the rhymer’s most disturbing songs.

On both his controversial and acclaimed albums, The Slim Shady LP (1999) and The Marshall Mathers LP (2000), Eminem raised eyebrows with the tracks “’97 Bonnie & Clyde” and “Kim,” respectively, in which he describes murdering his wife and disposing of her body.

“[‘Kim’] is like an outtake from one of our arguments in everyday life,” Eminem told MTV News of the song at the time. “We’ve had fights like that, where it’s like constant screaming and s**t like that. I basically took the anger that was built up from what she had done to me and what we was going through, and I made it into a song.”

Although the song was not intended to be taken literally, it harmed Kim’s mental health. Reports of Em and Kim’s infighting became widely publicized. Things came ahead after Eminem was arrested for felony assault and weapons charges after a June 2000 incident in which he allegedly pistol-whipped a man who kissed Kimb outside a nightclub in Warren, Mich. Then in July of that year, Kim made a suicide attempt at the couple’s home.

On Aug. 16, 2000, Eminem filed for divorce in Macomb County, Mich. According to the rapper’s rep, the couple had been separated since early June of that year, and Em decided that divorce was the only option. Five days later, on Aug. 21, 2000, Kim filed a $10 million lawsuit against the Grammy-winning artist, seeking full and permanent custody of Hailie and punitive damages for defamation. The couple eventually reached a settlement.

Interestingly, Eminem and Kim remarried in 2006, but filed for divorce four months later.

Watch Kimberly Mathers Talk About Her Tumultuous Relationship with Eminem Below

See Photos of Eminem From XXL‘s 25th Anniversary Issue Cover Story