Wynne is one of Hip-Hop’s most remarkable rising stars. Born Sina Wynne Holwerda in 1997, and growing up an outcast in Lake Oswego, a suburb of Portland, Oregon, she gravitated towards Hip-Hop at the age of nine. Studying the greats from afar, and dedicating her life to becoming a rapper by the age of 12, she established herself in the underground scene by competing in national cyphers. Soaking up influence from the greats of generations past (Jay-Z, Dilla, Foxy Brown, and the list goes on), as well as modern paragons like SZA and Drake, Wynne became a phenom by the age of 19, going viral several times and blowing the internet away with her veteran-level rapping. She quickly started gaining co-signs from some of music’s titans (Timbaland, Missy Elliot, Twista, Wyclef Jean) and cultural gatekeepers like Rob Markman and Zane Lowe, among several others. At 21 years old Wynne graduated college and released her debut mixtape “If I May..,” boasting assists from several A-list producers such as Hit-Boy, DJ Dahi, and Sounwave, as well as features from J.I.D, Mahalia, and fellow hometown hero, Damian Lillard. This took her on a sold out tour with Earthgang and Mick Jenkins at the top of 2020. Through the early 2020s, she dropped an experimental EP with Dreamville super-producer Christo, along with a dozen singles, garnering millions of streams as she shepherded fans towards her new sound, ending the year with a viral hit, “Look At You.”

Hailing from Rockwood, Portland, OR, Bocha is one of the gifted rappers on the frontlines of the budding Portland hip hop scene. He is a co-founder of Produce Organics, a Portland based brand, and artist collective.

When you look at his body of work, it’s hard to not see NE Portland hip-hop artist Donte Thomas as one to watch. Whether it’s battle rap, pop or R&B, working solo or in a group, Thomas always finds a way to stand out. Heavy drive, slick delivery and relatability have kept him relevant for years as he’s built his brand and progressed musically.

Penned as a journey of self-realization, reflection and growth, Ausar’s debut LP ‘I NOW KNOW’ set the city’s soundscape ablaze this past summer. Performing at Lyrical Lemonade’s coveted Summer Smash festival, Taste of Chicago as well as opening on tours for Chicago icons like Chance The Rapper, femdot., Joyce Wrice and others, the 26-year-old Windy City wordsmith’s live renditions of his latest record will leave you speechless. Be sure to catch fan-favorites like “Don’t Date Rappers,” “Spoiled” and “Win” live.