Fashawn was born in Fresno, California, where he had a rough childhood due to his father being incarcerated for a long period of time, while his single mother also dealt with a drug addiction. At eight years of age, Fashawn and his sister were both placed in a group home for sometime, before their Uncle Roy decided to take them into his custody as a father figure. Fashawn recalls writing his first rhyme at eight years old, and became fully engrossed in writing by the year 2000. In 2006, Fashawn released his first mixtape Grizzly City, catching the attention of fellow Fresno emcee Planet Asia who invited him to go on the road with him. Knowing the opportunity that presented him, Fashawn dropped out of school and pursued his dream. From 2007 to 2008, he established his presence throughout the Central California hip-hop scene, working with manager Aren Hekimian and releasing multiple mixtapes including The Phenom, Grizzly City 2, The Phenom 2, Higher Learning, and One Shot One Kill, which was put out by Orisue Clothing. One Shot One Kill was well-received by both fans and hip-hop websites, including 2DopeBoyz and DatPiff, gaining him more attention and momentum as an upcoming artist.

In 2009, Fashawn performed throughout the United States with various hip-hop acts, including separate tours with Ghostface Killah and The Grouch. On September 24, 2009, he released a project produced entirely by The Alchemist titled The Antidote to get fans hyped up for his debut solo album.

On October 22, 2009, Fashawn released his first full-length solo album titled Boy Meets World produced entirely by Exile. The album received critical acclaim, and Fashawn was praised for his ability to articulate the inner struggles and dreams of a young kid growing up in a tough environment. XXL Magazine gave the album an XL rating, concluding that "Boy Meets World is a strong debut from such a young MC, and it resonates a lot more than the work of some rappers decades his senior.” In March 2010, Fashawn graced the cover of XXL's Top 10 Freshmen issue, standing alongside Wiz Khalifa, J. Cole, Big Sean, Nipsey Hussle, Jay Rock, Freddie Gibbs, and others. This represented a prestigious benchmark for upcoming rappers who demonstrated great potential and success.

Between 2010 to 2011, Fashawn continued to embark on various tours with Wiz Khalifa, Talib Kweli, and Brother Ali. He also performed at the Paid Dues and Rock The Bells festivals alongside Blu and Exile. On February 16, 2011, he released a mixtape called Higher Learning Vol. 2, which spawned two videos, "Down That Road" and "Big Dreams" produced by J. Cole. Fashawn also created his own strain of medical marijuana which he coined Grizzly City Kush.

On September 25, 2012, Fashawn and underground hip-hop legend Murs released a collaborative album called This Generation. Fashawn and Murs performed many tracks together at various shows to help promote the album, including Rock The Bells 2012. On November 17, 2012, Fashawn organized a hip-hop festival in his hometown of Fresno, California called Grizzly Fest 2012, which featured performances by himself, Murs, Husalah, Strong Arm Steady and many local talent and skateboarders. On November 20, 2012, he released his eleventh mixtape Champagne and Styrofoam Cups which included the song "Medicine Man" featuring Wiz Khalifa.

In 2013, Fashawn continued to have a notable presence in various musical and mainstream outlets. He performed at various major hip-hop festivals such as Paid Dues, Rock the Bells, and Hip Hop Kemp where he joined Kendrick Lamar on stage for a duo freestyle session. On November 6, 2013, Fashawn released a video for a new song called "The Beginning", produced by Evidence and directed by both Evidence and Punit Dhesi. On December 9, 2013, Fashawn's artistry was the focus feature in a web episode of OTW Perspectives by Vans. On February 14, 2014, he released a new song "Ladies" for Valentine's Day, dedicating it to the women who struggle to stay strong and raise the next generation of kids.

On March 24, 2014, rap icon Nas brought out Fashawn during the Mass Appeal showcase at SXSW 2014 in Austin, Texas, where Fashawn performed a new song "Fuck the World" in front of the sold-out crowd.[10] During a Reddit "Ask Me Anything" session in 2014, Nas mentioned Fashawn as one of two contemporary artists that had recently caught his ear (the other artist being Bishop Nehru).

On April 12, 2014, during the infamous WBO welterweight title rematch Manny Pacquiao vs. Timothy Bradley II at the MGM Grand Garden Arena, the champion Timothy Bradley appointed Fashawn to lead him into the ring while performing "Champion" produced by Exile. "What I like about this is that it is real hip-hop," Bradley said in regards to Fashawn's big performance. "It is about heart and character, not about partying it up in a club or all that kind of stuff that so many records are about."

After years of anticipation, it was announced that Fashawn's second full-length solo album The Ecology would be released in the second half of 2014. In an April 2014 interview, Fashawn stated, "The Ecology has been a concept that started at least five years ago for me. I took the time to really work on this project because I knew that it would be important not just for my career, but for hip-hop. There could be no better time for all these blessings to be coming my way, and I'm just so happy to say that The Ecology will be coming out this year."

On June 9, 2014, a variety of media outlets reported that Fashawn had officially signed to Nas' Mass Appeal Records. "Fashawn is one of the most underrated in the game," Nas said in a statement. "The world is gonna know soon. We're excited to have him as a part of the family." Fashawn is scheduled to release The Ecology on September 30, 2014 on Mass Appeal Records.