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John O’Leary celebrates Jazz Appreciation Month with legendary musician Kevin Eubanks.

To celebrate Jazz Appreciation Month, I’m honored to welcome Kevin Eubanks, one of the most accomplished jazz musicians of his or any generation.

As a prolific guitarist and composer, Kevin is frequently recognized for his role as former Music Director of The Tonight Show band, appearing on The Tonight Show with Jay Leno for 18 years.

Yet it’s what led up to this iconic role that is most intriguing.

Today, Kevin shares about growing up with a strong musical influence, what it was like to hitchhike to gigs around Philadelphia at 13 years old and how he was able to overcome his shyness.

And I can’t forget to mention…Kevin shares a fantastic impersonation of Jay Leno that you don’t want to miss.

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  • Growing up in Philadelphia, Kevin’s dad was a police officer and his mom used her love of music to develop his confidence.
  • At 13 years old, Kevin was asked to join a neighborhood band at a show at the Chatterbox.
  • Always the youngest member of the band, Kevin didn’t learn to drive until he was 26.
  • Around 15 years old, Kevin realized he had a special talent.
  • Kevin would play with his back to the audience because he was so shy.
  • At the start of his 18-year run on The Tonight Show with Jay Leno, Kevin learned how to integrate music in ways that enhanced the show + engaged the audience.
  • From former Senator John McCain to comedian Robin Williams, Kevin found ways to connect with guests.
  • Kevin is most proud of making his parents proud as well as being a successful musician playing alongside iconic jazz artists before he joined The Tonight Show.


If you enjoyed hearing from a world-renowned jazz musician… you’ll love our Musician’s playlist. I’ve sat down with Journey’s Jonathan Cain, two-time Grammy winner Lauren Daigle and legendary entertainer John Tesh. I also sat down with viral country star Walker Hayes for episode 146 to talk about “behind the scenes” of country music but also about life, loss, love, sobriety, failing and trying again. I’ll have the link to all of these conversations at JohnOLearyInspires.com/podcast.


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  1. Q. What is the best book you’ve ever read?
    A. [I asked Kevin what the most impactful albums he's ever listened to.] Tracks by Oscar Peterson and The Inner Mounting Flame by Mahavishnu Orchestra
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. Being passionate about something, even if you’re not the best.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. Nothing but with the attitude of “it’s just a house”.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. The ocean.
  5. Q. What is the best advice you’ve ever received?
    A. If you can contribute, you’re worthy of being a human.
  6. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. Thank you, Mom and Dad.