Alyssa Flaherty on Singing for Kevin Costner, Taking Risks, & Using the Stage as a Game | Ep. 20 episode artwork

EPISODE · Sep 10, 2026 · 1H 31M

Alyssa Flaherty on Singing for Kevin Costner, Taking Risks, & Using the Stage as a Game | Ep. 20

from The Bilby + Ella Show · host BilbynElla

Our guest this week is singer-songwriter and artist Alyssa Flaherty, who grew up performing the national anthem at pro sporting events and singing at talent shows and charity events around Annapolis, Maryland, long before she ever picked up a guitar. At 14, she quietly cold-emailed a handful of Nashville labels, and only told her family once she got a response back. That leap of faith turned into a full family move to Nashville in March 2020, where Alyssa taught herself guitar, learned to write from scratch, and found her community at open mics in Leiper's Fork.In this episode, Alyssa tells the almost unbelievable story of how producer and Modern West band member Teddy Morgan discovered her at a writer's round and brought her in to sing "Amazing Grace" for Kevin Costner's film Horizon: An American Saga, an opportunity that led to her opening for Costner and his band on the road and finally pushed her to start releasing her own music. She gets honest about the real gap she sees in artist development across the industry, the hypocrisy of demanding authenticity while pushing artists toward sameness, and why she treats every show like a game she's trying to win against herself. She also opens up about faith, family, and how fearlessness looks different now than it did at 14.Whether you're an artist trying to find your own lane, someone who loves a good against-the-odds story, or just want to hear someone talk about music like it's still magic to them, we think you'll love this one.Check out Alyssa's newest singles "Texas in July" and "Falling for Someone," available everywhere you listen to music!0:00 – Welcome & Intro: Alyssa Flaherty0:53 – Reminiscing About Fox & Locke's Open Mic Scene9:52 – Growing Up Without a Musical Family & Voice Lessons at Best Buy13:09 – Classical Training, the National Anthem & Auditioning for The Voice16:01 – The Cold Email That Convinced Her Family to Move to Nashville21:22 – Learning What Nashville (and This Industry) Really Gives You24:05 – Learning Guitar, Writing Her First Songs & Meeting Teddy Morgan27:36 – The Call That Led to Singing "Amazing Grace" in Horizon: An American Saga29:02 – Her First Tour, Starting in Jackson Hole, Opening for Kevin Costner33:02 – The Hardest Part of Being an Artist & Nashville's Broken Development System38:49 – Advice to Her Younger Self & Getting Comfortable With the Unknown44:48 – Why Artist Development Takes a Team & How Its Absence Hurts the Music51:45 – The Voice, Staying True to Herself & Fearless Then vs. Now55:43 – Songwriting Came Naturally & How Attached She Gets to a Song59:07 – Chasing the "Shania Twain Effect" & Building Long-Term Artistry1:06:22 – Finding Melodies That Never Get Old & Capturing Ideas on the Go1:09:20 – Inside Her New EP, American Sweetheart, & Her Release Strategy1:10:47 – Bodies of Work vs. Instant Gratification in Today's Music1:13:49 – What Stays the Same When You Strip Away the Genre1:16:52 – Her Current Listening & Will We See Another Music Renaissance?1:27:37 – Closing Thoughts: Music as a Time Machine & Making Something That Outlives YouFollow Alyssa Flaherty:InstagramTikTokYouTubeFacebookFollow The Bilby + Ella Show:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Join Our Community⁠⁠⁠⁠⁠⁠Follow Hill:⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Willie:⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram

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Alyssa Flaherty on Singing for Kevin Costner, Taking Risks, & Using the Stage as a Game | Ep. 20

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