When Mason Jennings started writing songs for his new record, Songs From When We Met, he was in a setting he had never written in before. "I was living out at a farm for a month and walking through some old woods on the property every day. There was a river. And each day an owl would come find me, and then perch above me, day or night. I saw lots of snakes. Songs just came to me there. They were coming in so fast they just about took my head off. It was unlike anything I’ve experienced before,” recalls Jennings. In Native American animal medicine snakes symbolize rebirth, owls symbolize seeing what others cannot and turning darkness into light. Both are themes throughout the album and the music has a clear hopeful feeling.

 
Jennings produced his self-titled debut album in 1997 on a Tascam analog four-track in the living room of a rented home, playing all instruments himself. In October 1998, he began a weekly gig at Minneapolis' 400 Bar. The two-week gig ended up lasting four months. On November 12, 2013, he released Always Been. The first single from the album was "Lonely Street", was followed by "Wilderness". He released Wild Dark Metal in 2016. He got divorced and after taking some time off to focus on painting, to recover from depression and to heal from agoraphobia, he began touring again. He remarried in 2018 and released an album of love songs inspired by his new relationship, Songs From When We Met, available now.