Gangsta’s Paradise rapper Coolio died Wednesday at the age of 59. He was at his friend’s place in Los Angeles when he was found unresponsive.

Paramedics arrived at the scene and declared him dead.

Just like his music career, Coolio’s romances have also been in the spotlight. Here’s a history of his relationships.

When Coolio – born Artis Leon Ivey – rose to fame he was married to Josefa Salinas. The duo got married in 1996. Josefa also became popular as a media personality on the California radio station, KQIE-FM. The two have four children together, three daughters and one son.

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Coolio and Salinas ended their marriage in 2000. 

In 2009, he was romantically linked to Anabella Bellesi, and the two welcomed a son, Christopher.

Coolio is said to have had multiple children with different women. The rapper wasn’t very open about revealing about his children publicly. According to reports, his son with Bellesi is his 10th child.

The rapper also dated Mimi Ivey. Their relationship was featured in an episode of Celebrity Wife Swap. The episode, which aired on March 5, 2013, showed the couple swapping places with Sugar Ray frontman, Mark McGrath, and his wife, Carin Kingsland.

Regarding the experience, Mimi recalled to Women in Business:

“Although I loved Coolio with all my heart I was not happy with the state of our relationship at that time. We’ve had our challenges over the last couple of years just like any other relationship.

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“We have eleven kids between the two of us, two grandkids and two more on the way that keeps our home life exciting.”

She said of their relationship: “But on the other hand, we definitely work well together because we are able to separate business from our home life by always supporting each other professionally.

“I’ve always had my own light in the entertainment world, and this is why we are able to launch a collaborative venture together.”