Hopeful Monster began as a recording project at songwriter Jason Ball’s Nervous System studio in Seabright, Nova Scotia. Jason and studio partner Paul Aucoin of The Hylozoists spent the first few months of 2001 recording two albums: Hopeful Monster and The Hylozoists’ La Nouvelle Gauche, both released on Halifax's Brobdingnagian Records. In 2002, Hopeful Monster began playing shows in Halifax, and showcased at Pop Montreal and CFNY Nu Music Night at the Horseshoe Tavern in Toronto. Jason and Paul (on drums) were joined by Dale Murray on electric guitar and pedal steel, Andy Patil on bass, David Christensen on organ and flute and vocalist/vibraphonist Damien Moynihan.

In June 2003 Jason toured Norway and UK to promote a European release of Hopeful Monster on Norwegian indie label Hype City Recordings, traveling and performing with Sufjan Stevens, Emil Nikolaisen of Sereena Maneesh and label owner Frode Stromstad. While in Oslo, he was invited to play at the wedding party for Of Montreal's Kevin and Nina Barnes.

In 2004, Jason returned to Europe as a member of The Heavy Blinkers, opening shows with solo Hopeful Monster sets in Germany, France and UK. When his wife became pregnant with their first daughter in 2005, Jason stayed close to home, playing keyboards in the Hylozoists and with chanteuse Lily Frost, as well as harmonizing in vocal pop trio The Wilderness with fellow songwriters Andrew Rodriguez and Jason Kent.

Then for two years, the Ball family lived quietly in the Nova Scotia countryside. Jason branched out, teaching audio at a Halifax college and taking up the job of organist in a remote seaside church. In July 2007 the Balls hosted the first Mourning Dove Festival in their yard and living room.

Early in 2008, Jason and family moved to Toronto. A second Hopeful Monster album, Metatasking, was self-released at Toronto 's Horseshoe Tavern, in a limited edition, hand-decorated jacket; a new band line-up was introduced, featuring By Divine Right front man Jose Contreras on guitar, bassist Jeremy Little, drummer Gavin Maguire and keyboardist Jeff Heisholt. Metatasking was re-released in Canada on Gooseberry Records in 2009, and consists of tracks recorded with the original Halifax band members, as well as tracks recorded in Toronto with Jose and Gavin and members of The Wilderness and The Hylozoists.

Following Jason's 2008 solo return to the UK, Hopeful Monster appeared around Toronto in a variety of configurations, featuring Jason and Jose plus several others, swelling at times to a ten piece mini orchestra. In fall 2009, Jason embarked on a fruitful, six month hibernation, writing and arranging nearly two dozen songs for the third Hopeful Monster album. At the core of the recording are Jason on piano, Jose on electric guitar, violinist Randy Lee and cellist Alex McMaster.

In October 2010, Hopeful Monster was chosen to represent Nova Scotia in CBC Radio 2's Great Canadian Song Quest, for which an artist from each province and territory wrote and recorded a new, original song about a road selected by Canadians via the Song Quest website. Hopeful Monster's song "The End Of Road (Can't Believe It's Over Now)" celebrates No. 1 Highway, which runs through Nova Scotia's Annapolis valley.

In September 2012, the final mix sessions for the third Hopeful Monster album were concluded at Jose's Chicano Power studio in Caledon, Ontario. The product of a two-year collaboration, Beautiful Island was released in March 2013.