Wyatt Michael - Singer / Crooner (Sing With Swing / The Voice)

·1 hr 6 min·5 clips

Host Jeremy Swift recounts being mesmerized by Wyatt Michael's Sinatra tribute at a San Antonio jazz club.

Host Jeremy Swift introduces the episode by describing his personal experience seeing Wyatt Michael perform a Frank Sinatra tribute at a jazz club in San Antonio, praising Wyatt's vocal talent and stage presence. Wyatt shares his background, born in 1996 and raised in Fredericksburg, Virginia, as a homeschooled child of a Marine father. He initially played guitar in a rock band called Chasing Avenir with his brother Ed for over seven years, performing at venues like the National Theater in Richmond. Wyatt reveals his shift to jazz began at age 18 after hearing the song 'Call Me Irresponsible' in the Adam Sandler movie 'Click,' which led him to Michael Bublé and then Frank Sinatra. His first public jazz performance was in early 2019 at a bridal shop anniversary in Fredericksburg, where he sang tracks including 'Dream a Little Dream.' Wyatt discusses his regular gig at Amy's Cafe and performances at senior centers, sharing a poignant story about a fan named Dolores who passed away and left him Sinatra memorabilia. In 2021, he appeared on Season 21 of The Voice after casting directors contacted him; he auditioned with 'Mack the Knife' and had chairs turned by Kelly Clarkson and Ariana Grande, ultimately choosing Clarkson's team. Wyatt describes the reality show experience as limited in coaching, with his elimination occurring in the second round after a duet of 'Sunny.' He recently moved to Las Vegas in March 2025 for better jazz club opportunities and proximity to Los Angeles, though he still travels frequently for gigs. Wyatt talks about his original songs, including 'With You' from 2015 and tracks on his EP 'Just Two,' and mentions his website singwithswing.com. The episode concludes with details about his upcoming holiday shows in San Antonio and Houston in December 2025, promoting a Sinatra holiday songbook performance.

As heard by us

A focused musician interview about crooning, performance pressure, Sinatra, and The Voice.

Wyatt Michael's shift from rock-band frontman to crooner gives Fascination Street a clean center: a singer figuring out where his voice belongs.

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Why you'd press play

Hear Wyatt Michael trace the shift from rock-band comfort to solo crooning, Sinatra-style phrasing, and The Voice.

Read the full recommendation in PlayNext →

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