In the 20th episode of Guess That Record, Jackson interviews trumpet playing extraordinaire Barry Danielian! A long time member of the E Street Band with Bruce Springsteen, Barry and Jackson were able to record their conversation live in Calgary the day before The Boss rocked the Stampede City. Barry has been a member of the E Street Band since 2012, performing in stadiums all over the world and appearing on multiple Springsteen albums including "The Promise," "Western Stars," and "Only the Strong Survive." Barry has also collaborated with Billy Joel, Sting, Elton John, and many more. In the episode, Jackson and Barry speak about their mutual music connections, and what it's like to be on the road with the E Street Band.

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