[1][3] Henwood authored and illustrated a series of children's books that were published by Farrar, Straus and Giroux in the late 1980s and early 1990s, including A Piece of Luck (1990) and The Troubled Village (1991).
He produced and directed Alice, a short film scored by Barry Adamson, and created a second magazine of the same name, which "chronicles how childhood is represented in art and the media".
Pop singer Rihanna enlisted Henwood as the creative director for 2009's Rated R. He designed the logo and conceived the brand and styling of the album, videos and TV spots.
[5] Art publisher Rizzoli released a photo book documenting Henwood's work for the pop star in 2010, entitled Rihanna: The Last Girl on Earth.
[5][6] Henwood also painted the cover of his then-girlfriend Róisín Murphy's album Ruby Blue and its EPs and singles, in addition to directing the music videos for "If We're in Love", "Sow into You" and "Movie Star."