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.
Songs From When We Met pulls you in from the start, with Jennings telling the listener, "Get into my car now...let's leave the city". “Cursive Prayers is the first song I wrote for the album. I hadn’t written anything in a long time and any time I tried writing things I wrote were very dark. This song is so hopeful and full of love it surprised me. I think it was the beginning of things getting better in my life, like a message from another dimension."
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.
In early 2008, Mason signed with Jack Johnson's record label, Brushfire Records. Jennings released In the Ever in May 2008. The title was inspired by his son referring to where he was before he was born as, "In the ever". Blood of Man soon followed and received a coveted 4-Star review in Rolling Stone, who also cited, “What makes Mason Jennings one of the best singer songwriters you’ve never heard of is his ragged intimate voice and his simple ruminations on God, war, hope and gratitude.”
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.