• Sam Fleming


Wintertime changed the game then disappeared. There are rumors that he has been hiding out in Iceland, and other rumors that he just no longer cares about the rap game. His self-titled album was released in 2017 but since then he hasn’t been heard from. This mysterious personality is part of what makes Wintertime’s music so endlessly engaging. You never really get a sense of who Wintertime is as a person, but he paints a wild and shadowy picture of himself as an artist. Wintertime operates like a parka-draped, comic book villain who makes music only for inhabitants of the South pole. His self-titled project was his thesis statement and the last project he left for us until he returns from his hideout.

In the world Wintertime constructs on this album it’s “wintertime all the time 365… 366 on a leap-year” as he makes clear on the self-titled song “Wintertime.” On the album cover, he poses on top of a Toboggan sled being led by four huskies, gliding through snow-covered bluffs. The instrumentals he chooses to rap over echo this iciness; each synth sounds absolutely crisp and the drums are completely dried out. It is by no means an experimental project, but the way that Wintertime’s vocals glide in and out these songs exude weirdness.

On his self-titled project, Wintertime creates his own world that sounds lost somewhere out in the universe. He takes the idea of cloud-rap and extends the genre label into something completely different than originally intended. Rather than his vocals being obscured by the beats, his vocals dance on top of the glitz and glam of the instrumentals. Each track highlights the quirkiness of his music and the oddness of his personality.

“U Times 2” is the early standout from the album. On the song, Wintertime mixes a laid back, almost lazy, flow with more melodic elements. Of course, he references his coat made in Canada and how cold he is, but the hook is when Wintertime takes it up a notch. He sings, “I’m like that, in my style, the way I slide is like wowwww… I’m you, times two.” This type of humblebrag is common on this project. Even though “you times two” means absolutely nothing in real life, on this album it’s meaning is absolutely intact.

With adlibs appearing like “splendid” and “nice” this project always maintains a feeling of goofiness. Wintertime says he could have played for more than one NBA team, first referencing the Suns and later the Jazz, but it only ever seems like he’s talking shit. The listener is not meant to take anything he says too seriously which makes the entire project such an easy and refreshing listen. It is always my go-to project when I need a little bit of joy.

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