The realization that summer is over can be difficult to take in. Even for those who relish in the colder months, fall can represent more than just a dip in temperature. It’s the kickoff to what some call “cuffing season,” the annual period when, faced with the disappearance of sunshine, people settle down with a significant other. The opposite can also be true. Summer love comes to an end in the fall, leaving you alone in a cold, empty apartment. Drake, the 30-year-old rapper from Toronto, makes music for both scenarios. The rapper’s label, October’s Very Own, may as well be a clearinghouse for autumnal vibes. This week, a set of Drake singles to cozy up with alone, or not.
Picture it: You’re wearing a cashmere cardigan, it’s crispy outside, the leaves have all been infused with color. You inexplicably find yourself scrolling through pictures from 2015, when you and the proverbial ex were still together. Where has the time gone? You wonder. Naturally, there is a Drake song for this moment. Released as a loose single preceding his 2012 record Take Care, his single “Club Paradise” laments lost love in the way that only a man can, which is to say completely one-dimensionally. But fall can be a lonely period that warrants personalized introspection. Drake is scratching the surface of his own issues here, and if you find yourself singing along on a cold autumn morning, you might find some answers about yourself, too.
Drake opens “My Side,” a bonus track from 2015’s If You’re Reading This It’s Too Late, by describing the song’s ethereal production (courtesy of Boi 1da and Drake’s in-house producer Noah “40” Shebib). “This sounds like what being rich feels like,” he boasts. Drake is always shielding himself with his success but here, on one of his more vulnerable tracks, the subtle brag serves a different purpose. “My Side” unfolds like an extended therapy session with Drake effectively disarming himself in a quest for answers. “Keep in touch with other women cuz’ you made me nervous,” he laments. A personal truth wrapped in a humble brag. Despite Drake’s description, “My Side” sounds more like what being hopeless and in love feels like.
Sooner Than Later
Listening to Drake’s earlier work, when his boasts were born out of ambition instead of reality, a certain tenderness is present that doesn’t appear on his more recent songs. “Sooner Than Later,” a cut from his perfectly autumnal 2007 mixtape Comeback Season, sets a foundation for the lady problems Drake will face for the entirety of his career. The poor guy just doesn’t know how to settle down. Here, years before Rihanna or Serena or the host of other women who Aubrey Graham has been publicly linked with, he seems genuinely concerned.