John Leventhal thinks his initial, preanalytical ideas are the good ones. John Leventhal realized that there “really is no daddy, there isn’t anybody who really has it all together, knows all the answers. You’re kind of in the wilderness. You have to take a chance to fail.” John Leventhal isn’t sure how to measure success. John Leventhal is a self invented guy.

Despite his five Grammys, his critically and commercially successful work as musician, producer, songwriter, and recording engineer who has produced albums for William Bell, Michelle Branch, Rosanne Cash, Marc Cohn, Shawn Colvin, Rodney Crowell, Joan Osborne, Loudon Wainwright III, and many others, he’s still wondering if he’s made it.

As a musician he has worked with these artists as well as Jackson Browne, Willie Nelson, Bruce Hornsby, Elvis Costello, Dolly Parton, Emmylou Harris, Charlie Haden, David Crosby, Levon Helm, Edie Brickell, Paul Simon, Patty Larkin, Susan Tedeschi, the Tedeschi Trucks Band, Steve Forbert, Kelly Willis, Donald Fagen, and Johnny Cash.

As a songwriter he has had over 150 songs recorded by various artists, including Rosanne Cash, Shawn Colvin, Marc Cohn, Michelle Branch, The Tedeschi Trucks Band, Vince Gill, George Strait, Shelby Lynne, Patty Loveless, Joe Cocker and William Bell.

We met over the summer met in his Manhattan studio, which occupies one floor of the home he shares with his wife, singer-songwriter Rosanne Cash. We talked about his process in the studio, how he developed his own personal approach to making music, and why even the simplest questions can have complicated answers.

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