Episode 315: Winnetka Music Festival Series Part 1 featuring Ben Kweller

I was at Winnetka Music Festival June 19-20, where I spoke to @benkweller, a multi-genre multi-instrumentalist, whose very personal and revealing songwriting has been his trademark throughout his more than 20-year career. This episode is Part 1 of a four-part series of in-person interviews from the Winnetka Music Fest, and I’ll be featuring these throughout this and the following week.

Ben’s latest album, Cover the Mirrors, is not only a personal documentation of his life, but also a tribute to his son Dorian, who died tragically in 2023. Ben’s vulnerability and authenticity are on full display in this recent effort, and he talks to me about just how his songwriting plays a critical part in his life — and how it especially helped him during a time of unimaginable sorrow. 

This is a heartwrenching yet hopeful story of perseverance and grace. Ben’s humor and joyful spirit is on full display in this lively conversation, and I’m honored to have sat down with him just prior to his set. I can’t wait for you to give this one a listen!!

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Chapters:

00:00 -- Episode Intro with Host Josh Rosenberg

06:30 — Intro and joking around about an apparent show mix-up

07:10 — Ben’s vulnerability as a songwriter and communicator

08:16 — Why plainspoken lyrics can still feel powerful

09:50 — DIY instincts, business, and being direct

11:31 — The loss of Dorian and how music stopped at home

12:56 — Writing songs to communicate with Dorian

14:38 — The story behind “Oh Dorian”

16:56 — How the song shifted into a friend’s perspective

18:02 — The emotional weight of the album Cover the Mirrors

19:06 — Fiction, first person, and writing from lived truth

20:56 — How tragedy changed the impact of Ben’s songwriting

21:49 — Fans supporting Ben on tour through grief

22:38 — Feeling Dorian’s presence on stage

23:37 — Creative momentum and working on a new album

24:48 — Showing up for the muse and the creative life

25:29 — Songs as something received, not just written

25:59 — The French phrase in a new song and checking the translation

27:47 — Flow state, openness, and the idea of receiving songs

29:28 — How listeners interpret Ben’s lyrics

30:26 — Songs that took on new meaning after Dorian’s death

31:19 — Ben’s musical beginnings as a kid

33:49 — His music-first writing process and melodic math

35:54 — Free will, destiny, and the shape of a life

36:32 — Being Jewish, family traditions, and Shabbat

38:15 — Shared cultural identity and appreciation for Jewish guests

38:47 — Johnny/Modern Love Child and collaboration

39:49 — Reissue news for On My Way

40:37 — The next studio album, Agarita

41:37 — Wanting a teleprompter for live shows

42:30 — Thoughts on lyric stands and authenticity on stage

43:22 — Daniel Johnston and outsider music

43:53 — Roger Greenwald and producing a debut album

45:45 — Artists as conduits and creating a unique path

46:33 — Closing thanks and tribute

46:50 -- Episode Wrap-up with Host Josh Rosenberg

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Roadcase theme music: "Eugene (Instrumental)" by Waltzer