Hemingway was born to Harry Hemingway, a lorry driver and local comedian on the club circuit, and Flo Hemingway, who was one of Hull's best-known barmaids. In Hull's Henry Cooper School, Hemingway was in the same class as The Housemartins' future drummer, Hugh Whitaker. The two shared an interest in drumming, and one day, when the class were asked who would like to learn drums, they put their hands up first. Hemingway followed Whitaker into bands, first the Newpolitans with Dave Rotheray on bass, and then the Velvetones. Whilst at university in London Dave was drummer and a founding member of The Shoppers. It became a well regarded post-punk band (Steve Brain guitar/ lead vocals Maxine Tarte keyboards/ vocals Gavin Hearne lead guitar/vocals Christos Yanni bass/ vocals). Dave's drumming skills can be heard on their first demo.
Hemingway's first solo album, Hello Cruel World, was released as a download only on iTunes. The album's title was inspired by Hemingway's experience recording in the capital.
After forming "The South" a tribute band in 2008, Hemingway along with Alison Wheeler, Gaz Turtles and more from the original Beautiful South line-up, are releasing their first album since 2006 entitled Sweet Refrains.