Y'lan Noel looks back at the complicated relationship.

Add Yahoo as a preferred source to see more of our stories on Google. When HBO's groundbreaking series “Insecure” premiered in 2016, nobody could have predicted that some of its most memorable moments ...

After weeks (or possibly months) of no contact, Issa (Issa Rae) and Lawrence (Jay Ellis) were forced to be in the same room together. The bitter exes finally faced off at a birthday party for their ...

Issa Rae and Prentice Penny are revisiting the world of Insecure through a new podcast celebrating the legacy of the acclaimed HBO series. Released through Rae’s HOORAE media company, BLOCC PARTY: An ...

"I got hacked on Twitter," Rae recalled, "and somebody was like, 'I'll help you if you give me three more seasons of ...

Issa Rae was the first black female host for the CFDA Awards. In one of her hosting moments the comedian brought up the impact black culture has had on fashion. Rae said designers use to 'make black ...