Jenny Lewis is contemplating why, despite being one of the most critically acclaimed and downright treasured songwriters of the last 25 years, she’s never tasted mainstream success.

“I may have a little bit of the indie rock self-defeating, foot-shooting thing,” she concedes. “You’re talking to your girl that changed a [Rilo Kiley] song that should have been called Bad News to Portions For Foxes. Terrible idea! I wanted the poetry but everyone was like, ‘You’re crazy’.

“It’s just part of ...