Born and raised in Port Huron, Michigan, William Ronald Simpson III became a fan of music at a very young age. Being exposed to various genres such as Motown, Country, and Classic Rock, his interest peaked with the different sounds and melodies that came from the songs his parents played in the car and around the house. But it wasn’t until his mom played him select Eminem songs that he fell in love with rap, and after that introduction, there was no slowing him down. Becoming known as the kid in school who could rap any verse in songs, especially the faster-paced ones, Dolla Bill acquired his stage name from his aunt and aunt’s friend while on a trip up north. After being dared to rap Eminem’s widely known fast song Rap God and succeeding, Dolla’s aunt and her friend decided he should take on the name Dolla Bill, as it was a fun play off of his real name, Billy. Not too long after this trip, Dolla’s friends at school also began referring to him as Dolla Bill, without knowledge of the nickname his aunt and her friend had given him. From there, he knew the name was there to stay.

Garnering a following at his high school as well as neighboring schools in the district, Dolla Bill went on to release multiple singles and projects on his SoundCloud, most notably the Simpson EP and Mind At 16. Having accomplished this before the start of his senior year, many fans and fellow classmates encouraged Dolla to not only continue on with his musical journey, but to also upload his music to streaming platforms, and that he did. In October 2018, Dolla Bill released his first streaming single titled Rip It which was met with overwhelming praise from his peers.

From 2018 through 2020, multiple singles were released on both streaming platforms and SoundCloud, including fan favorites such as Work, Jupiter, and FuckwitMe. In April of 2021, Dolla Bill finally released his first commercial EP titled Nightmare On North Street. The release received widespread acclaim from fans across the United States, and proved how versatile the Port Huron rapper could be given that the project sounded nothing like his previous efforts. With the success and support of his first project, Dolla went on to release weekly songs for the entire summer of 2021 in a series he called Dolla Days. The collection of releases, each one sounding different than the last, created traction for the rapper in parts of the world outside of the United States due to all of the different producers he was working with for the series. Many fans considered some of the songs his very best, and declared the idea an overall success.

More recently in 2022, Dolla Bill released two EPs titled When The Moon Turns Green and House Sitting, as well as the mixtape Cooped Up Sessions 3, another installment of his growing mixtape series. Each project captured different emotions and headspaces as well as different songwriting abilities, which is what many consider to be what makes Dolla’s music so special. With each release, the listener goes in knowing that they won’t know what the music sounds like until they press play.