How Alec Benjamin's 'Let Me Down Slowly' Took Him From Sidewalk Performances to the Hot 100 (and Beyond)

Alex Currie
Alec Benjamin

In the past few months, Alec Benjamin has collaborated with Alessia Cara, performed on The Late Late Show With James Corden, and hung out with his idol, John Mayer. Most recently, the 24-year-old singer landed his first song on the Billboard Hot 100, with his vulnerable breakout hit “Let Me Down Slowly.” But getting to this point in his career wasn't as simple as it may seem.

After landing a record deal at just 18 years old, Benjamin was dropped from the label before even releasing an album. Determined to make his music career happen, Benjamin began playing on sidewalks and outside of venues around the world, handing out business cards to help build his fan base. Befriending Jon Bellion during a co-write in 2016, Benjamin toured with the "All Time Low" singer later that year, but continued his parking lot busking to make sure he was doing all that he could.

"I've played pretty much everywhere. One of the cool things about music is you get to meet a lot of interesting people along the way. You can pick up fans on social media, but they're faceless -- you don't get to know the people," Benjamin tells Billboard. "I got into music because I liked the human connection, so that's one of the reasons why I was compelled to go outside of venues. It kept me inspired."

Benjamin wrote "Let Me Down Slowly" in 2017, inspired by an experience with an ex-girlfriend. It was one of the songs that caught the attention of Atlantic Records later that year, and he officially signed his second record deal in February 2018. Since then, Benjamin has released a 12-song mixtape titled Narrated For You and sold out two headlining tours, ultimately proving that a second chance is always possible if you put your mind to it.

As "Let Me Down Slowly" continues making waves, Benjamin chatted with Billboard about his first Hot 100 hit and what the song -- as well as his perseverance -- has done for him.

How did you react to hitting the Hot 100?

I called my mom, and then I did a breakdance. When you pick a career like music that’s a bit unorthodox, it’s hard to tell if you’re on the right path. This is not like graduating or anything, but at least it [feels like] I’m doing something right.

How did Alessia end up on this version of “Let Me Down Slowly”?

She said that she liked [the song] on Twitter, so I sent her my phone number. I said, “Want to do a verse?” Two days later, she sent me a voice memo she recorded at home. You can record her voice on an iPhone and it sounds as good as anything. She added a lot of really cool harmonies, and her perspective brought new meaning to the song.

Isn’t social media how you linked up with John Mayer too?

Jensen Karp at KROQ found my music and sent it to John, and John really liked it, so he started posting about it. Then I sent John a message on Instagram like, “That's crazy.” But I realized I had sent him a message eight months before being like “Yo, I'm a huge fan, I love you, hope that I can meet you one day.”

He's always been one of my number one inspirations for making music in general, so it’s one of the coolest things that’s ever happened to me. For me, there's having your song on Billboard, and John Mayer talking about your music. That's pretty much it. [Laughs.]

Has he given you any advice since you’ve been friends?

Yeah, I've learned a lot from him. I was texting him about tour life and trying to figure it out mentally, [asking] him “How do you balance everything?” He was giving me tips about the road, songwriting and all that good stuff.

I talk to him all the time, actually. He sent me a bunch of voice memos of new song ideas.

Have you dropped into any other artist’s DMs lately?

I hit up Khalid on Twitter, and I worked with him a few weeks ago. I don't know if the song we had will come out, but it was pretty cool getting to work with him. I love his music.

What did you learn from your experiences playing on streets and outside of venues?

Everyone has to start somewhere, and it doesn't really matter where you start. I think it's important to build from the ground up and never be ashamed of playing outside of a venue. Just because you're starting outside of a venue doesn't mean that's where you're going to be forever.

What advice would you give someone who may have gone through a similar experience of being dropped from a label?

If you believe in yourself and you love making music, it doesn't matter what the situation is. You shouldn't give up -- you should always keep going and work as hard as you can, and keep writing songs, because you never know what can happen. Especially nowadays, you have a lot of control over your own destiny. Getting dropped from a label in 2019 is not a death sentence. Sometimes it can be the best thing that's ever happened to you.

I don't really feel like I'm in a position to give advice. I'm still taking advice from people, and I’m still figuring it out. I kind of just put things in the music. People are like how do you feel about x, y and z -- I’d rather talk about it in my music. But I certainly shouldn’t be giving relationship advice.

A version of this article originally appeared in the Feb. 16 issue of Billboard.

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