Jesse Sky

Episode 001 / November 22nd, 2026

Jesse Sky is a singer-songwriter, longtime friend, karaoke enthusiast, and one of those people who somehow makes a room feel a little more fun just by being in it.

He and Jeffery go way back, and their friendship is full of music, stories, laughs, and probably a few things that are better left off the internet.

As a songwriter and performer, Jesse brings that same honesty and personality to his music, making him the perfect person to kick off Scott Free!

Good friend. Great songwriter. Brother from another mother.

And, fittingly, the very first guest on Scott Free.