Released in 2018, Big Red Machine's self-titled debut album evolved from improvisation and what Dessner calls "structured experimentalism," with an ear toward building tracks that would work well in a live setting alongside visual elements. Dessner’s generous spirit and desire to push music forward has never been more deeply felt than on Big Red Machine's "How Long Do You Think It's Gonna Last?," the second album from Dessner's ever-morphing project with Bon Iver's Justin Vernon. Songs feature guest vocals and writing contributions from artist friends including Fleet Foxes' Robin Pecknold ("Phoenix"), Ben Howard and This Is The Kit ("June's a River"), Naeem ("Easy to Sabotage'), Sharon Van Etten, Lisa Hannigan and My Brightest Diamond's Shara Nova ("Hutch," a tune inspired by Dessner's late friend, Frightened Rabbit frontman Scott Hutchison) and Taylor Swift herself ("Birch" and "Renegade,").