My introduction to Caleborate would have been through the same way that it was for many of his fans: I read a comment that he made on a YouTube video. His honesty, vulnerability and young adult perspective made him a favourite artist of mine during my late high school years. I would proclaim Caleborate as my favourite rapper to my friends.

It was an instant connection when I first heard his song “Anna’s Lament”. I was 15-years-old at the time meaning I was far away from personally relating to lines such as “it was two times; three if we counting that time I got hard then went soft” but I still enjoyed the inherent coolness and self-assuredness he displayed on the track. The first mixtape of his that I heard, #theusual, had everything that I needed to believe that Caleborate would eventually become a genuine star when it came out in 2014. He had a confident charisma, good beat selection, solid hooks, generalised subject matter, impressive music videos, social media presence and anything else. I set the #theusual artwork as my phone’s wallpaper.

I remember the excitement that I had when he randomly dropped his next mixtape, Winter Break, at the start of 2015 and I could hear the progression from his last work. “Mom’s Advice” was incredible to me and I used to play “Next Semester: The Ride Home” with its extensive “Last Call”-type outro when I too rode home on the bus. I felt so assured Caleborate was the next one that I shared my belief that “@Caleborate is one of the most promising hip hop artists out there” in an early tweet.

Caleborate had embraced an alternative style in both image and sound until this point so I was amazed by the versatility when he released “El Portal” in mid-2015 and sounded like a mix of Kendrick Lamar on “Backseat Freestyle” and Joey Bada$$ on “Christ Conscious”. His first album, Hella Good, came out a month later and I was thinking that this was the break that would put him out there as one of the future stars. “From the Eastbay with Love” was the reason for the sudden incorporation of filtered vocals in my productions. “Get the Green” was getting heavy play in my DJ sets. “SMH” was unlike anything I had ever heard before. “The World” was my reason for getting confidence back when it was lost.

1993 came out in 2016 and I had to believe this would be the album that would be it. Real Person was released the next year and it was an incredible effort for an independent artist. After the first break in his career, Caleborate released his fourth album Light Hit My Skin a few years later in 2021. It contains the songs “Untitled (Hit Record)” and “Pull Up” that are among the high points of his output.

It is ten years since I first found Caleborate and he is still making music, still independent and still worthy of far more attention than he has ever received. I remember following the trajectory of his career and having no doubt in my mind that he was on the path to something great. The artist who believed in himself so much to propel oneself from YouTube comment sections to much more gave me every desire to be able to claim that I too had equal belief before anybody else. Through it all, he never lost the intimate nature of his lyrics that bare the vulnerabilities, misgivings and mistakes that initially drew me to becoming more than a fan.

Caleborate’s “Thought It Was” is a realisation that his life might not have been what he thought it would be. My 15-year-old self feels the same way.