The most recent installment of our 500 Greatest Songs podcast examines Aubrey Graham’s pinnacle performance as a sophisticated R&B vocalist and established pop icon.

Drake has always been a magnet for attention. His strange journey has taken him from teen fame on Degrassi to blockbuster rap stardom. In 2024, his beef with Kendrick Lamar has blown up into one of the all-time biggest hip-hop beefs. They went from zero to 100 real quick, sending deadly insults and accusations back and forth. Yet he’s also the Drake the pop icon, the certified loverboy who sings emo ballads like the 2015 classic “Hotline Bling.”

On Rolling Stone’s list of the 500 Greatest Songs of All Time, Drake scored three songs: “Hold On, We’re Coming Home” at #129, “Take Care” with Rihanna at #269, and “Hotline Bling” at #373. He goes into full-on Quiet Storm mode for “Hotline Bling,” pining over an ex who’s doing fine without him, now that she’s wearing less and going out more. It became a Number Two hit, and it’s never left the radio since.

“Hotline Bling” is Aubrey Graham the smooth R&B singer—but it came out in the period when he was working hard to establish his rap cred. In 2015, he surprised everybody with the purist moves of If You’re Reading This It’s Too Late, then dusted off Meek Mill in one of the century’s great rap battles. He also teamed up with Future for their quickie collabo, What a Time To Be Alive. When “Hotline Bling” dropped, it felt like a victory lap—after a year of hip-hop flexes, he felt confident enough to sing his most vulnerable soul ballad.

Obviously, in 2024, Drake is in a totally different place. He hasn’t been in his feelings over his exes’ vacation photos lately. Instead, he’s caught up in a rap beef of historic proportions. He and Kendrick have been firing diss records at each other since March, from Drake’s “Push Ups” to K-Dot’s “Euphoria.” Within minutes of Drake dropping “Family Matters,” Kendrick rushed out his reply “Meet the Grahams.” But Drake couldn’t come back from the knockout punch of “Not Like Us.” The battle seems to be over now, but many experts are calling it a disastrous L for Aubrey. The Drake going up against Kendrick is a world away from the R&B smoothie of “Hotline Bling.” Or IS he? The question is: does this beef mark the end of an era for Drake? Or does it mean the end of Drake?