Is ‘Hotline Bling’ Drake’s Greatest Song?

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?

On this week’s episode of Rolling Stone’s 500 Greatest Songs, hosts Rob Sheffield and Brittany Spanos discuss Drake’s career, “Hotline Bling,” and the Kendrick beef. They’re joined by their brilliant colleague Jeff Ihaza to talk about “Hotline Bling” and its place in the Drake story. Jeff breaks down the context of Drake’s hip-hop status in 2015, and how that influenced how the world heard “Hotline Bling.”

In 2004, Rolling Stone launched its 500 Greatest Songs of All Time list. Tabulated from a massive vote that had artists, industry figures, and critics weighing in, the list has been a source of conversation, inspiration, and controversy for two decades. It’s one of the most popular, influential, and argued-over features the magazine has ever done.

So we set out to make it even bigger, better, and fresher. In 2021, we completely overhauled our 500 Songs list, with a whole new batch of voters from all over the music map. Rolling Stone’s 500 Greatest Songs takes a closer look at the entries on our list. Made in partnership with iHeart, Rolling Stone’s 500 Greatest Songs finds Brittany and Rob discussing a new song each week, delving into its history and impact with the help of a special guest — including fellow RS colleagues, producers, and the artists themselves. It’s our celebration of the greatest songs ever made — and a breakdown of what makes them so great.

Check out the latest episode above, on iHeart, or wherever you get your podcasts, and look for new episodes every Wednesday.