At a college that prides itself on creative types, counting Robert Lowell ’40, Paul Newman ’49 H’61, Allison Janney ’82, Walk the Moon, Pinegrove, John Green ’00 and others among its alumni, Will Oakley ’20, quiet but determined, is striking his own path towards critical acclaim as an artist and musician.
Oakley’s music and visual art embody the contrasts and contradictions upon which his identity is formed. Oakley resents fame, money, social media and modern society in general. All the while, he is relentlessly ambitious and in dogged pursuit of musical acclaim.
He said that music is not his passion, per se, explaining that the thing he really enjoys is being outside and playing sports. “Music is more something that I need to do,” he told the Collegian.
Oakley’s latest music is on Spotify, while Soundcloud has music dating back to the spring of his first year at Kenyon. He also has an album under the name Lilyoung $till Dumb, which is titled Clout Chasing 101 on Spotify and Soundcloud User #859910524 on Soundcloud.
His two latest releases, titled “Paradise Falls” and “Stressless,” are singles that reflect his maturation as an artist. Both are four-minute tracks characterized by a melodic refrain and some simple verse, playing on the same theme of escaping the stress of everyday life.
In “Paradise Falls,” the escape is in the form of a relationship that removes worry about the future. “We could pause again, we’ve just got today,” he sings. It begins with a favorite sample of Oakley’s music: an excerpt from Toy Story of Woody saying, “reach for the stars.” Both works are melancholic and wistful, putting Oakley’s talented production, rapping, singing and lyricism on full display. While Oakley likes these two recent songs, he feels that they embody a more calculated approach to music-making: They are part of his short-term plan of making popular music in hopes of going viral.
“The way I see it, I have no connections, I hate promoting myself and I don’t like to perform, so there’s no chance I’m going to gradually build a music career through normal means … I’m going to have to do what I call the Post Malone approach, which is [that] I’ll try to make as many catchy songs as possible in hopes that one of them catches on and some teens on TikTok do a stupid dance,” he said.
Oakley’s side project, Lilyoung $till Dumb, garnered attention nine months ago when he released the album Soundcloud User #859910524. The opening track, “Ok Google, Play Lilyoung $till Dumb,” begins with a sample of David Bowie arguing that the internet is chaotic, nihilistic and subversive. The sample is overlaid with J.S. Bach’s “Toccata and Fugue in D Minor.”
“I think we’re actually on the cusp of something exhilarating and terrifying,” Bowie says before Lilyoung finally enters with his aggressive, fast-paced style. The album ends with a long, dark monologue by Oakley at the end, which joins Bowie’s in theorizing about the nihilism and alienation of modern society.
“I spent the first eight songs just kind of capping and bragging about all sorts of stuff that I haven’t actually done, and then I decided to put the last monologue in at the end as a moment of honesty to contrast with all of the blatant lies throughout the rest of the album,” Oakley said. “And actually, people tend to gravitate towards the honest moments the most.”
The album’s art on Spotify is based on Dr. Suess’s The Sneetches, with one Sneetch standing above the rest with a Twitter-verified badge. The album’s lyricism is a tongue-in-cheek mockery of fame culture. As Lilyoung argues on the opening track of the album, it’s all fake: “I can autotune my pictures, Photoshop my lines,” he raps.
Oakley’s inspiration for the Lilyoung $till Dumb persona was, like Walk the Moon’s “Anna Sun,” inspired by a summer at Kenyon. In contrast to Walk the Moon, though, Oakley related his summer experience to the Stanley Kubrich film The Shining.
Oakley’s most popular song by far, though, is a cover of Taylor Swift’s “Nice to Have a Friend” that he released under his own name, which has over 2,400 plays on Soundcloud. The track, titled “Friend in You,” adds some lyrics and an improved bassline to the Swift song.
“I was kind of waiting for the drums to hit [when I first heard the song] and it never did, so I was like, ‘okay, let’s put some drums in it,’” Oakley said.
During an icebreaker session on the first night of orientation as a first year student, Will Oakley boldly proclaimed to the room that he had a “fire mixtape dropping soon.” Oakley, who wore a “Hillary for President” T-shirt with either gym shorts or sweatpants almost every day of his first year in college, calls that time the lowest point in his life, but also a breakthrough in terms of his creative output. “Ideas just started pouring in and I was just trying to write everything down,” he recalled. Oakley has since deleted music from the first semester of his first year, saying it was not only bad, but overly political.
In high school, Oakley said he would sit for hours trying to come up with lyrics, brainstorming wordplay. “I was a musician before I was an artist, meaning I started rapping before I had anything to rap about,” Oakley said. Despite having nothing to rap about, Oakley recalled that while in high school, it was still a novelty to have a Soundcloud.
Oakley decided he wanted to be a rapper after seeing the music video for Eminem’s “My Name Is” at the age of 13. He felt empowered by rap’s boldness. He names Eminem, Outkast and Frank Ocean among his influences. His biggest influence, though, is Kanye West. Eminem, Kendrick Lamar and other great rappers are craftsmen, Oakley says, but Kanye is, as Oakley terms it, a “creative.”
“If I had an idol, it’d probably be him. Ideally, my ultimate dream [is that] I want to be a multi-dimensional creative, as in singing, rapping, producing, doing visual art, architecture, film, being able to do everything, kind of the way he’s doing,” Oakley said.
Oakley aspires to authenticity in his creative projects. He doesn’t want to create something for the sake of the craft or to mimic something else. He seeks out space to be original, which he believes is hampered by the structure of schooling.
“Every year, the political science department [Oakley’s major] is [teaching] the same books, and that makes me wonder if my knowledge is the exact same as every other political science major that has left here, so I definitely enjoy coming up with something kind of unique, and I also enjoy being a contrarian and stating the unpopular opinion,” he said.
One of those opinions is the “anti-book theory,” which contends that film and music have effectively displaced the book as means of instruction and storytelling. Most popular among his friends, though, is the “baller-non-baller theory,” which is specifically a theory of masculine personalities at Kenyon that he derived when he quit the baseball team and joined cross country. “Ballers” are the hypermasculine jock types, while “non-ballers” are more sensitive and reserved.
As for his avid people watching, Oakley said one can only question where the herd is going from the outside. Speaking more frankly, Oakley said, “I like judging people. I’m a pretty judgemental person, no doubt about it.”
Oakley produces and paints in the same setting that he comes up with these theories: alone in his room. He characterizes his creative process as a necessary act that borders between therapy and toil.
“I definitely have a conflicted relationship with creating. It’s not something that I want to do or enjoy doing, but more something I feel I need to do,” he said. Much of creating music is being hunched over a computer, adjusting the vocals and high hats in an audio-editing program. That, to Oakley, is not fun.
“I usually cannot sleep if I don’t do a few hours of creative work before,” Oakley said, adding after a pause that, “In some ideal world, if I was perfectly content, I probably wouldn’t be doing music.” He said that people understate the degree to which suffering and art go hand in hand, arguing that great art is inspired either by an artist’s own struggles or their ability to perceive and sing about the suffering of others.
Oakley recalls childhood, specifically around the age of 12, as the period in his life when he was truly content. Back then, he says he drew or sang without any pressure or desire to finish or share a creative project. Childhood isn’t the only image from the past that Oakley looks to with rose-colored glasses. He believes that humans were happiest when they were hunter-gatherers.
“I think since the Agricultural Revolution, human history has just been a sequence of people inventing things to solve problems while creating new problems in the process,” Oakley said. He says the fact that great art would not exist is a sacrifice he is “willing to make.”
He jokes about starting a hunter-gatherer cult in Alaska. If he had to pick between being anonymous or famous, though, he would choose the latter. “I definitely want to say what I’ve got to say and I want to be heard,” he said.
What that means is that Oakley does want to make great art. He believes that art serves the purpose of helping one escape the present or enter into a happier place in their mind, but truly great art shifts the way one thinks about the world. For Oakley, the classic example of this is the 1998 film The Truman Show, starring Jim Carey.
Oakley’s biggest gripe with his creative process is that he feels that sometimes he overemphasizes the suffering aspect.
“Sometimes I felt like I caught myself almost doing things that I knew would make me sad because it would produce more inspiration,” he said.
Oakley says that in the midst of the pandemic, without the on-campus pressure to go out and have fun, he doesn’t face that dilemma. In an email, he wrote, “It’s not just me this time. People are copying my style.”
To capture his thoughts on the coronavirus and social distancing, Oakley is working on a three-song EP. Oakley, who only releases music on Wednesdays, expects to release the EP on May 6. One should expect the style of these new songs to follow right in line with “Stressless” and “Paradise Falls.” It remains to be seen if these are the songs that will be the songs that a teen on TikTok dances to, launching Oakley’s rise to stardom. Nonetheless, the new music will be streamable on Soundcloud and Spotify.