“Generation Why” is the first single from Conan Gray’s debut EP "Sunset Season". The song was announced on September 30th, 2018 via social media along with an 11-second teaser music video. Conan released the song and its music video on October 3rd, 2018. After being accepted into UCLA and moving to Los Angeles, Conan signed a record label deal with Republic Records, and like the rest of Sunset Season, Generation Why features an evolved style and greater level of production as a result.

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