Tales from the Checkered Backpack is Dezzy's debut ablum. The album is a collection of stories and songs inspired by Dezzy's personal experiences. Specifically, speaks on trauma, addiction, and navigating it all.

This is a testimonial album that does not hold back. It features a mix of acoustic and hip-hop elements that blend together to create a unique sound. The album has received critical acclaim and has been praised for its honest and heartfelt lyrics.

The album cover shows Dezzy sitting on the floor in a bookstore. A book titled "The War" is purposefully shown to depict the challenges and difficulties he faced in his life.