One of the enduring paradoxes of jazz is that it can be one of the most adventurous and free-form of all kinds of music — yet, in many quarters, it also remains stubbornly sexist and socially conservative. There are still jazz venues in this town that are de facto boys’ clubs, where months go by before a female instrumentalist appears on the bandstand. And for transgender musicians, the barriers can be even higher.

It’s not like Jennifer Leitham is a dilettante or amateur. Raised John Leitham in Reading, Pennsylvania, the upright bassist moved from Philadelphia to L.A. in 1983 and built a prolific career backing such legendary figures as Peggy Lee and George Shearing, as well as working for many years with Mel Tormé and Doc Severinsen. Besides being an especially versatile, dexterous bassist, Leitham is also a composer, teacher and singer who fronts her own groups and has released 10 albums.

“The more outspoken I am

But she was never happy as John Leitham. “Everyone’s story is different,” she says. “I knew early on I was put in the wrong group, that I felt an incongruence.”

She began transitioning to her true female identity by adopting the name Jennifer, which was suggested by Leitham’s ex-wife. Eventually, she underwent gender-reassignment surgery — which, for her, turned out to be an unusually difficult and risky process in which she nearly lost her life due to medical complications. But Leitham soon found out that her biggest challenge would be getting friends and colleagues to accept her as Jennifer.

“My coming out was a kind of kaleidoscopic event,” Leitham says. “When you first transition, the people around you transition.” She boldly decided to reveal her new persona publicly while on tour in 2001 with Severinsen, who, to his credit, stood by his longtime bassist. Many others were not as understanding.

“I thought my career was over,” she says. “The more outspoken I am, the more I speak out about transgender issues, the more the jazz community shies away from me.”

Leitham was still able to get gigs in clubs, but she stopped being invited on the more lucrative festival circuit. “In jazz, a lot of the moneyed interests that make the festivals are a pretty conservative bunch,” she notes.

Then her 2006 contemporary jazz album — a purposeful statement of identity aptly titled The Real Me — ended up becoming her best-selling CD. A fascinating 2012 documentary about her life, I Stand Corrected, was a hit at international film festivals, and the 63-year-old bassist was spotlighted last year in Vanity Fair’s “Trans America” issue. Her most recent recording was 2015’s Mood (S)wings, a moodily diverse album of love and loss whose “octo-entendre” title alludes to her sister’s battle with depression.

“My art is my most important thing,” Leitham says. “I’m an activist to some degree … but I think I do more good in the world by writing portraits of myself as more than my gender.”

Despite the ongoing obstacles, she says she has no regrets about making her transition. “How can I regret it? I wouldn’t be alive.”

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