Josh Redman | Photo by Jay Blakesberg

The idea of recording an album of ballads has been on Joshua Redman’s mind as long as he’s been making records. Though he’s undertaken a number of different projects over the course of his career, it’s taken the 44-year-old saxophonist twenty years to actually fulfill that particular goal.

“I’ve always loved playing ballads and thought that I would want to do a ballad album of my own someday,” Redman says. “As a jazz musician, you’re very exposed playing a ballad. Everything happens slowly in a ballad, so everything is on full display: every nuance, every imperfection, every subtlety in your phrasing and your sound is right there in the open. It takes a certain amount of control and experience with your instrument and musical maturity to be able to pull that off. And you’re also exposed emotionally because playing a ballad you really have to dig deep, so you have to have a certain amount of vulnerability and life experience. I didn’t feel quite ready twenty years ago. I’m not sure I was totally ready this time, but I was definitely more ready.”

The result is Walking Shadows (Nonesuch), which complements Redman’s stellar quartet – featuring pianist Brad Mehldau, bassist Larry Grenadier, and drummer Brian Blade – with a small string orchestra, thereby tackling two daunting traditions at once. A number of jazz musicians have attempted to play with strings over the decades, only a select few managing to avoid being dragged down by mawkish or pedestrian arrangements.

Redman cites a number of influential models that struck the right balance, including classics by Clifford Brown, Ben Webster, and Stan Getz, as well as more modern attempts by the likes of Wynton Marsalis. The most well-known and divisive example of the form has long been Charlie Parker with Strings, the legendary saxophonist’s 1950 release. “I love that record, but I’m not crazy about the string arrangements,” says Redman, echoing a popular sentiment about the session. “I think that there’s a certain tension between the modernity and immediacy and rawness of Bird’s playing and what I think is at times a bit of old-fashioned sentimentality in the string writing. But there’s so much beauty that comes out of that, the way that Bird can just soar. He sounds inspired and so free and so melodic, even in the context of string writing that’s maybe not ideal.”

Working in conjunction with frequent collaborator Mehldau, Redman chose a surprisingly wide-ranging repertoire. There are the expected jazz and American Songbook standards, like “Easy Living,” “Lush Life,” and “Stardust.” But alongside those familiar tunes are Bach’s “Adagio,” a Beatles classic, “Let It Be,” and songs by John Mayer and Blonde Redhead.

Redman and Mehldau had worked together previously on the pianist’s own jazz-plus-orchestra project Highway Rider, but the Walking Shadows session was still a relatively alien experience for the saxophonist. He’ll be on more familiar ground at the Annenberg Center on Saturday, where he’ll lead his current touring quartet of pianist Aaron Goldberg, bassist Reuben Rogers, and drummer Gregory Hutchinson. The tour reprises Redman’s main touring band from 1998 to 2001; while the various members have continued to work together in different combinations, the full quartet has only reassembled this year. “Because we’ve been playing together for so long, there’s a tremendous amount of familiarity and trust and empathy among us,” Redman says. “I think that gives us the space and the freedom to really take chances. This particular band has never sounded better.”

Redman was born into the world of music. His father was the great free jazz saxophonist Dewey Redman, who worked extensively with Ornette Coleman and Keith Jarrett. He was raised in Berkely, California by his mother, dancer and librarian Renee Shedroff. He originally had no plans to follow in his father’s footsteps, planning instead to attend Yale Law School. But in 1991 he took a year off to move to Brooklyn and instantly became active on the fertile New York jazz scene, winning the Thelonious Monk International Jazz Saxophone Competition that year.

He released his self-titled debut CD in 1993, earning his first Grammy nomination. He’s explored a variety of contexts in the decades since, from his groove-oriented Elastic trio to the Sonny Rollins-inspired pianoless trio of Back East or the shifting combinations of a double trio on 2009’s Compass. Redman spent seven years as the artistic director of SFJAZZ, the San Francisco-based jazz presenting organization, and the first director of its all-star band, the SFJAZZ Collective. In recent years he’s also collaborated with the irreverent piano trio The Bad Plus, played in duo settings with Brad Mehldau, and co-founded the collective quartet James Farm with pianist Aaron Parks, bassist Matt Penman, and drummer Eric Harland.

His current quartet reunited after several years of concentrating on various permutations of the pianoless trio for his main outlet as a leader. The change reflects Redman’s ongoing desire to continually find new settings and challenges. “I’d like to think that’s adventurousness,” he says. “Some people might say that it’s a sign of restlessness. To me, the best jazz is made by bands, not by individuals, and I certainly love playing in the same band over a period of time, really growing and developing the music. But I’m also in a phase now where I enjoy being part of a number of bands at the same time, moving from one project to another. It keeps me on my toes musically, keeps me challenged and inspired and it keeps things fresh. Maybe there’ll come a time when I settle into one thing and do that for ten years straight, but maybe I haven’t grown up yet.”

At the Annenberg show, Redman’s quartet will perform a mixture of old and new, including originals penned for the band, jazz standards, and ballads from Walking Shadows. While he won’t have the string orchestra on stage, Redman says that lessons he learned while recording with the chamber orchestra will come to bear on even his small group playing.

“To me, the key to playing a ballad is the key to playing jazz in general. It’s a combination of relaxation and focus, relaxation and intensity. And that’s something that I try to have when I play small group. I love the energy, the directness, the immediacy and the excitement of playing live, but I think that there should always be a kind of relaxation, a softness and a gentleness in the background, whether we’re playing a ballad or not. I’m not saying that’s something that I achieve regularly, but it’s definitely something that I strive for.”

Joshua Redman performs at the Annenberg Center for the Performing Arts, Saturday, November 9th. Go here for tickets and more information.