Jared Benjamin had wanted to play the Plain White T’s “Hey There Delilah” on guitar since he was a kid.
“I tried five or six times from the time I was 10 to the time I was 20, but it just never stuck,” he says.
Then, the pandemic gave him enough time to try again and, eventually, he got it. Benjamin branched out from there, playing covers of Hozier and Ed Sheeran songs.
Covers were fun at first, until he no longer had an interest in playing other artists’ songs.
He asked himself, “Why don’t I just start writing them?”
“I fell in love with writing more than I fell in love with music at first,” he says.
His passion for music was clear, even though he had established plans to become a lawyer. So much so that his mom submitted his application for Berklee NYC on his behalf — without him knowing.
“I had started the application months in advance, and so I’d filled out a lot of the stuff but I never pressed submit,” he says. Benjamin used his mom’s laptop for the application, and the tab stayed open long enough for her to submit it.
The one-year master’s program taught Benjamin that less is more. It also allowed him to lean further into his dramatic storytelling — something he says didn’t fit with his history, philosophy and politics majors in undergrad.
“I would do a lot of writing for those majors and I would never get good grades because I would always just dramatize the history,” he says.
Now, dramatization is his specialty. He won’t tell you he loves you, but he’ll tell you he needs you more than oxygen.
His appreciation for the written word influences his music-making process.
“I usually just take a guitar and find four chords and then just start riffing ideas,” he says.
Some songs come together in 15 minutes. Others take Benjamin and his collaborators anywhere from a few weeks to a few months depending on the rewrites.
His releases over the years have been leading up to his album, ICARUS, and its expanded version, ICARUS: Too Close to the Sun.
“This is the first body of work that I’ve really put thought into when it comes to themes and ideas. It’s more than just one song at a time,” he says. “This project as a whole has made me feel very grounded and cemented in who I am and what I want to be.”
One of Benjamin’s proudest moments on the album is the song “Sue,” named after his grandmother.
“It’s about my grandfather and his battle with dementia and the fact that he can’t remember anything anymore, but he could still remember my grandmother,” he says.
“I’ve never seen my grandmother cry before, and I had never seen a song of mine connect with my family like that.”
Benjamin’s music is also connecting with listeners around the world, thanks in part to #BookTok — the segment of TikTok devoted to literature.
Benjamin didn’t know what it was.
A friend of his, Jenna, told him that his song “Three Steps Ahead” was the perfect fit for the romance novel “Fourth Wing.”

He listened to her advice and posted a few videos referencing the characters in the book.
The reading community has since propelled “Three Steps Ahead” to more than 13 million streams since its release in January.
“It has fundamentally shifted the people that listen to my music, the reach of my music, everything,” he says of the online reading community. “It has been such an insane thing to see, and I’m so grateful for it because it just gives me so much more passion for what I’m doing.”
And while Benjamin is grateful for the community social media has brought him, he’s also seeking to get people off apps like TikTok and Instagram, he says.
Instead of putting his trust in the algorithm to deliver his message to fans, he’s building his own infrastructure on Discord where fans can interact with him and each other.
“It’s become such a game, social media. It’s no longer that you post a song and it works. Now, you have to juggle and do a backflip and eat fire and potentially stab yourself with a sword and then tell people what’s going on.”
Here’s what Benjamin has going on: he just wrapped the North American leg of his debut headlining tour. He takes the “Icarus” tour to Europe and the United Kingdom this fall. And he’s continuing to build his Discord community.
“Having 5,000 Discord members, to me, is more important than having half a million followers,” he says.
Don't miss the next story: Subscribe to the Hollywood Rebound newsletter for free interviews and features on the artists shaping entertainment.