Working with his cousin Jason Madison, Kennedy released his debut mixtape album 25th Hour in 2008, instantly producing a buzz throughout the south side of L.A. In particular, the song "Watermelon Sundae" was widely played on local radio stations and performed live throughout the area, bringing more attention to Kennedy's music ambitions. Around this time, Kennedy's cousin Madison was a film student at Loyola Marymount University, sparking the beginning importance of visuals in Kennedy's later projects.
After his 25th Hour debut, Kennedy released 2 additional mixtapes in 2009; Best After Bobby (the title referring to "Bobby" Robert Kennedy), and Future Street/Drug Sounds. For the Best After Bobby mixtape, Kennedy collaborated with West Coast heavy hitter DJ Sour Milk and the Los Angeles Leakers, producing an instant buzz in underground circles across the country. Within the first hours of dropping the mixtape, Kennedy amassed over 10,000 downloads, officially solidifying his name among some of the top rappers in L.A.
However, with the release of From the Westside With Love in 2010, Kennedy became a major hit throughout the underground hip hop scene L.A. Gaining over 100,000 internet downloads, Kennedy began receiving praise from many established figures within the game. As reported by Texas based, major music festival South by Southwest, "Dom Kennedy has been verbally endorsed by many, including The Hundreds, Kenny Burns, Rick Ross, Taz Arnod of Sa-Ra, 9th Wonder, Murs, The Game, Justice League, DJ Mormile, Alchemist (producer), and Don Cannon just to name a few". With the success of From the Westside With Love, Kennedy became a major player on the independent circuit, traveling for performances throughout and outside the country; including a show in Dijibouti, Africa. Kennedy also began releasing an extensive amount of visual material at this time, including From the Westside With Love music videos for songs such as "1997", "Locals Only", and "The 4 Heartbeatz".
In early 2011, Kennedy released his 5th studio mixtape The Original Dom Kennedy, a tape meant to reflect Kennedy's individuality and sound as an artist. In an interview with MTV News reporter James Lacsina, Kennedy described the project as something that was a testament to himself in the rap game as well as the city he proudly represents:
"...with The Original Dom Kennedy, it was a time for me to take a stand in music. The way we grew up and our lifestyle, being kids from the inner city of Los Angeles. I just felt like that was missing,"