He first met Hal when they were both at the 1991 Winnipeg Folk Festival, Doug as performer with Robin Holcomb, Hal as an invited guest. The first recording session with the visionary producer was working on Hal’s second Kurt Weill project “September Songs” in ’94. This was with Anthony Coleman’s Selfhaters Orchestra – accompanying William Burroughs for the Brecht/Weill song “What Keeps Mankind Alive”. A few years later he was part of the horn section (with Steven Bernstein as arranger) and featured soloist for two of Lou Reed’s later records that Hal produced “Ecstasy” and “The Raven”. He was part of the house band for Marianne Faithful’s album “Easy Come, Easy Go” that Hal produced in 2008. He also participated in some of Hal’s shows which reimagined the work of a particular artist – two for Neil Young as a player and arranger, Nino Rota and Shel Silverstein as player, and Daniel Lanois as music director, player and arranger which was part of Toronto’s 2014 Luminato Festival.As well, he one of three music directors/ arrangers/ conductors, and part of the band, for the 2017 Leonard Cohen memorial tribute concert in Montreal – Tower of Song, filmed by CBC. In 2005, Hal asked him to be music co-ordinator, musician, arranger and conductor for Robert Wilson’s “In the Evening at Koi Pond” for the Expo in Aichi, Japan. In 2019 he contributed his signature “looped clarinet” to one of Hal’s last recording sessions – a version of the Velvet Underground song “Sunday Morning” sung by Michael Stipe.