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Studio Milwaukee Session: Kara Jackson

Jen Ellis

In April, Kara Jackson released her debut album, Why Does the Earth Give Us People to Love? Almost eight months later, she’s starting to see it land on several “best of 2023” lists as she wraps up a run of shows with Angel Olsen and gets ready for another one with Jamila Woods.

And to think it might not have happened if not for an insistent friend and a nice note from a neighbor.

We were very pleased to welcome Jackson for a Studio Milwaukee Session that put her rich voice and deft guitarwork center stage about 16 hours after she opened for Olsen at Turner Hall Ballroom. During our mid-set interview, she shared how interventions from those two people at a neighborhood block party helped get her where she is today.

“My best friend who I always played with on my block — we’d play Barbies and sing — she was like, ‘You have to sing at this open mic.’ And I was like, ‘Absolutely not,’” Jackson recalled. “Then she dragged me onto the stage in front of the microphone, and my neighbor who happens to play at the CSO emailed my mom the next morning and was like, ‘Your daughter can actually really sing.’”

Knocking out an Ella Fitzgerald selection in front of friends and family set her on the path to our Walker’s Point studios (and beyond, obviously) for a deeply felt acoustic performance that spanned decades. After starting with a cover of Karen Dalton’s 1969 song “Right, Wrong or Ready,” she sandwiched the interview with two songs from her album that both offer a look at love gone sideways.

Before wrapping up with “pawnshop,” Jackson explained how her affinity for secondhand items intersected with her romantic entanglements and led to a moment of self-realization.

“I think thrifting and especially vintage clothes, which I love, always remind me that there’s not a shelf life on someone’s appreciation for something,” she said. “Someone can uncover, like clothes, they can uncover you and find value in you. So you should never let someone else decide that you’re easily discarded.”

Enjoy Jackson’s Studio Milwaukee Session using the player at the top of the page, flip through the gallery below, and book a spot at all of our sessions by becoming a Radio Milwaukee member.

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Set list

  1. “Right, Wrong or Ready” (Karen Dalton cover)
  2. “no fun”
  3. “pawnshop”