When discussing personality in pop music, it’s impossible to disregard Tyler, the Creator. The loud-mouthed ‘rapper’ is a symbol of self-confidence, progressive Hip-Hop, and acting like a nutter on stage. His progression from controversial misfit to genre-bending maverick is one of the most interesting career arcs in modern music. The self-titled ‘Flower Boy’ conveyed himself as a satanic ‘Goblin’, and led to him being banned from performing in both New Zealand and the UK, his intentionally inciteful lyrics officially considered a ‘threat to public order.’ 

His career was built on shock factor. His breakthrough song ‘Yonkers,’ touches on suicide, wearing women’s underwear, and killing Bruno Mars, his success largely riding on the image of him eating a live cockroach in its accompanying music video. Tyler was polarizing, his early work described as ‘violently anti-gay and misogynistic’ by LGBTQ+ organization GLAAD, music critics simultaneously praising its provocative lyrics and non-conforming messages. Today, this image of a homophobic hellraiser is unrecognizable, the now openly bisexual artist exploring sexuality and love in his latest album IGOR. The self-produced blend of soul, jazz and hip-hop won ‘Best Rap Album’ at the 2020 Grammys.

He’s traded Satan for sunflowers, but continues to push boundaries; his anti-establishment ideals explored through experimental fashion design and music production, the polarizing figure now universally respected, his rejection of boundaries meeting critical acclaim.