I truly believe that Ryan Oakes is one of the most underrated rappers in the game. Every time he drops a new song, I listen to it for about 30 seconds and say to myself, “Yep, he did it again,” as I add it to my playlist. I discovered Ryan through his song “Hellboy” about six years ago, and he’s been in my daily rotation ever since.
Something I really admire about Ryan, more so after this conversation, is that he never waited around for anyone’s approval, and he certainly didn’t ask for permission. He decided he was going to make it, and then he went out and proved it.
While he’s the first to admit that people told him his music career wouldn’t work out when he gave up everything to pursue it, their doubt only fueled his drive even more. While so many artists nowadays are blending genres to create their own sound, few are doing it quite as well as Ryan. As stubborn as he was about proving those doubters wrong, he’s just as stubborn about not fitting into a one-size-fits-all genre box. He blends sharp-as-nails lyricism with unapologetic honesty, hard-hitting hip-hop bars, and infectious alt-rock hooks. You can hear how well he’s perfected it like a fine art form on his latest single, “Shin Splints,” from his forthcoming album, Scary Stories After Dark.
I’ve been wanting to sit down with Ryan for years, so this conversation was a particularly special one for me. After years of listening to his music, I finally got to pick his brain about the journey that brought him here, the risks he’s taken along the way, and what it means to remain relatable and human in an increasingly AI-obsessed world.
