Classic Conversations

Pop culture influencers, TV stars, film actors, comedians, and musicians share inspirational stories about the road to success. Insightful conversations that are part comedy/part drama and always entertaining! With your host, described as “The Midwest Lounge Letterman,” Jeff Dwoskin.


episode 167: Bits and Bobs and Judy Garland with Debbie Wileman

Following in the footsteps of Judy, Barbra, and Gaga, Debbie Wileman seems to be creating her very own A Star is Born story.

Over the pandemic, Wileman began singing “A Song A Day” and posting videos of timeless songs on Facebook. With over one million views later, she became an internet sensation with global fans. Following two sold-out performances in November 2021 in London starring in Little Massive Voice, Wileman won the audience award for “Best Vocalist” with the Broadway World Cabaret Awards.

My guest, Debbie Wileman and I discuss:

  • Debbie's background and early aspirations of being a singer
  • How the pandemic re-ignited her passion for singing to help entertain her friends lonely at home alone during lock-in
  • How Debbie decided to sign a song a day on Facebook
  • Going viral singing as Judy Garland with the help of a Judy Garland Facebook group
  • Being signed by an agent in LA (America)
  • Recording the album "I'm Still Here" - a collection of songs song as Judy Garland
  • Landing her first USA date at Carnegie Hall singing as Judy Garland for the 100th celebration of Judy Garland
  • Touring as Judy Garland

You're going to love my conversation with Debbie Wileman

Our Guest, Debbie Wileman

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  • Facebook

Hashtag Fun: Jeff dives into recent trends and reads some of his favorite tweets from trending hashtags. The hashtag featured in this episode is #PandemicBandNames from @CrossyPondTags. Tweets featured on the show are retweeted at @JeffDwoskinShow

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 2022-09-22  48m