Born in Bromham, Bedfordshire in 1974, Berry graduated with a degree in contemporary arts from Nottingham Trent University, where he regularly performed in several bands. Starting his career as a runner, he then became a presenter for a video game magazine show before concentrating on comedy, landing roles in cult show Garth Marenghi's Dark Place, The Mighty Boosh, and his most famous role, Douglas Reynholm in The I.T. Crowd. After writing and starring in his own comedy show, Snuff Box, he appeared in episodes of The Sarah Silverman Show and the promo video for Super Furry Animals' "Runaway," and fronted the spoof Save the Workers charity appeal for Adult Swim.

Berry continued to juggle his musical ambitions with his TV work, penning the musical theater parody AD/BC: A Rock Opera, for Channel 4, composing music for Saxondale, The Peter Serafinowicz Show, and sketch show Blunder, and releasing his self-funded debut album, Opium, for free through his website in 2008. After appearing in the films Moon and The Devil's Chair, and hosting his own slot on Absolute Radio, he signed to Acid Jazz Records, where he recorded and played every instrument on his '70s prog-folk-rock-inspired sophomore album, Witchazel. Featuring vocals from Paul McCartney ("Rain Came Down"), it was released in 2011 on the back of a U.K. tour with his Brighton-based experimental backing band Jonas 3, and a collaboration with the Bluetones' frontman, Mark Morriss, under the guise of the Swedish Twins. Berry followed up the album in 2013 with the release of the richly autumnal Kill the Wolf, which featured guest spots from Morriss, Eric Johnson of the Shins, and James Robert Shaw of Everything Everything. He remained busy afterward with his TV series Toast of London, but found time in 2014 to release an old-school, synthesizer-led new age album, Music for Insomniacs. The next year he took his band, now called the Maypoles, on the road, documenting it with a live album, titled Matt Berry & the Maypoles Live, that November.

When it came time to record his next album, 2016's The Small Hours, Berry headed to Rimshot Studio in Kent, where they used a hand-built 60-year-old mixing desk. He also used his home studio and for the first time recorded his band laying down the basic tracks live. Once they were finished, Berry took the songs home to add vocals and instrumental overdubs himself. Guest musicians on the record included horn players Ben Castle and Steve Jourdonas, as well as longtime backing vocalist Cecilia Fage. ~ Jon O'Brien