A cultural icon with platinum-winning albums (Doggy Style went 4x platinum and The Doggfather went 2x platinum), Snoop Dogg has been a beloved figure since he debuted in 1993. Originally a rapper/songwriter/producer, he has crossed over into celebrity pop culture, appearing in cult classic shows like The L Word, Entourage, and Comedy Central Roasts. He has developed and produced his own movies and TV shows, including Oscar-winning Training Day and VH1's Martha & Snoop's Potluck Dinner Party. An active entrepreneur, Snoop Dogg launched a cannabis-focused venture capital fund, Casa Verde Capital, as well as a cannabis lifestyle brand, Merry Jane, in October 2015. Snoop wrote a cookbook and published a follow-up calendar, and Merry Jane published a series of three CBD books (Merry Jane's The CBD Solution: Wellness, Sex, and Living) with Chronicle Books.

E-40 is a Bay Area rapper with twenty-eight albums, a founding member of the group The Click, and the founder of Sick Wid It Records. His 2006 single "Tell Me When to Go" was one of the first singles to popularize ghost-riding and the hyphy movement on a national level. In addition to his prolific music career, he owns tequila, bourbon, and vodka companies, as well as Filipino food company Lumpia. He has nearly two million followers on Instagram.