This week on Olay & Friends, we talk about how Nicki Minaj, Drake, and Lil Wayne — three icons of an entire era — have all been going out sad. From messy online antics to desperate rollouts and declining public goodwill, we break down how each of them fumbled their legacy in different ways. We get into ego, entitlement, aging in hip-hop, and why watching our former favorites spiral says as much about the culture as it does about them.

Chapters:0:00 Intro1:13 Hello!/Bit of a Slow Media Week7:13 Nicki Going Toe to Toe With MORE Unassuming Parties11:57 Bringing Her Humanity Into All of This15:16 List of Slighted People Around Niki21:34 Did Lil Wayne Feel Slighted???24:25 "It's Dusty!"30:05 No One Else Can Be Successful32:45 Not Legacy, But Simple Relevancy45:56 The Criminal Partner Issue56:26 Kenneth Reacts58:45 Nicki Might Not Be A Fashion Girl1:04:59 "Check It Out" React