Guest Stars Chinaza Uche as Henry Sophie Zucker as Abby Kevin Yee as Toshiaki Allegra Heart as Abiah Darlene Hunt as Maggie Gus Birney as Jane Humphreys Finn Jones as Samuel Bowles Pico Alexander as Henry "Ship" Shipley Ayo Edebiri as Hattie Wiz Khalifa as Death Will Pullen as "Nobody" Ade Otukoya as Henry "Box" Brown Nick Kroll as Edgar Allan Poe Co Starring Erin Gerasimovich as Anna Neville Lee as Clara Jamel Davall Rodriguez as Freddie Damani Van Rensalier as Dancer Jason Williams as Dancer Imani Wisdom as Dancer Wade Watson as Dancer Bethany Puente as Dancer Nerita McFarlane as Dancer Marley Lubin as Dancer Antonio Harvey as Dancer Marquis Floyd as Dancer Shawn Alynda Fisher as Dancer Chloe Campbell as Dancer Kenny Bermudez as Dancer Anthony Auguste as Dancer Tatiana Barber as Activist / Dancer Braeden Brickner as Newspaper Boy Tim Simon as Townie 2 Omar Shaukat as Townie 1