At 5:45 p.m. in San Francisco’s Caffe Trieste, vestiges of the Beat Generation are alive and well. A gray-haired bohemian in a weathered felt hat—half-mast eyes, impish grin—hunches in the corner over what looks to be his 17th beer of the day. Under a wall of black-and-white photographs of Neal Cassady and Jack Kerouac, a wizened professor lectures two students on why they should burn their copies of One Hundred Years of Solitude.

Thirty-seven-year-old jazzman Joshua Redman navigates the crowd with his first coffee of the day and sits by a window overlooking Grant Avenue. He’s wearing a baseball hat, blue zip-up, and sneakers—and appears more like a college student than one of the most prodigious jazz saxophonists playing today.

In fact, Redman was on his way to becoming a law student before he took time off in 1991 to play jazz in New York City. Since that watershed year, he’s recorded 11 chart-topping albums for Warner Brothers—his latest, Back East, was released in April. This new album pays tribute to influences like Sonny Rollins and Wayne Shorter, and is another tome in
the modern jazz renaissance he helped usher in.

Redman is modest, even insecure at times, and quick to take himself down a notch when speaking of his success. He never had a formal music education, and one has to wonder if circumventing that institution allowed him to roam the jazz landscape—from traditional to funk and rock to free jazz—as effortlessly as he does.

“I’ve always put myself in situations where I felt I was in over my head, musically,” he says. “I played with musicians who were way better than I am. And I just learned by doing.”

Redman finishes his coffee and slides a shopping bag of dress shirts under his chair. He doesn’t shop often but when he does, he says, it’s an undertaking. He’s compulsive about size. Even if a shirt fits perfectly, he has to try on the size below and the one above to make sure he’s got the right one.

It’s fantasy to think you can accurately track a musician’s development, but it seemed to take Redman time to find the right fit in jazz as well. Critics questioned whether the 24-year old media darling was ready for his rapid rise to fame in the early ’90s. It wasn’t until 2001 and the critically acclaimed Passage of Time that the young star seemed to find his groove.

Comparisons are difficult. (They usually are in jazz. It’s supposed to be an original art.) A blend of Rollins and John Coltrane hits close to the mark, but, really, Redman’s sound is his own. On Back East he records with a stripped-down acoustic trio, just bass and drums, for the first time ever. The album is a wonderful mosaic of traditional swing, Asian melody, and contemporary jazz. The sparse rhythm section, drawn from New York City musicians, showcases Redman’s work on tenor and soprano saxophones. The album is his most exciting recording to date and smacks more of a response to his influences than a redux of their music.

“To the extent that my influences are there, I think it’s in a natural and organic way,” he says. “I’ve never been someone who’s been able to sound like someone else. Now, I hope, it’s starting to become a sound that has more weight and depth and maturity to it.”

He was already accepted at Yale Law School—after graduating summa cum laude from Harvard and achieving a perfect score on his LSATs—when he took a year off to play in New York.

The sun is dropping over North Beach, so we walk down Columbus Avenue to look at some of the old haunts where, in the 1950s, the Beats delivered the message of bebop to the world. Redman stops under a three-story mural of Benny Goodman and other jazz greats, and tells me about growing up in Berkeley with his mother, dancer Renee Shedroff. Finances were tight and Redman focused more on studying and securing a steady job than on music. His mother exposed him to all kinds of music, and at age 10 he picked up the tenor saxophone. The choice was a probable one as his father, Dewey Redman, had been one of the legendary “tough Texas tenors” who came out of Fort Worth in the ’40s.

Redman joined the jazz bands at Berkeley High School and Harvard, and also played with Berklee College of Music students during summer breaks in Boston; but he rarely saw his father growing up and played with him only occasionally. He was already accepted at Yale Law School in 1991—after graduating summa cum laude in social studies from Harvard and achieving a perfect score on his LSATs—when he took a year off to play in New York.

Part of the reason Redman had never fully embraced music was a hesitancy to embark on the itinerant musician’s life his father had led. But when he started playing sideman in his father’s band in ’91—as well as getting calls to gig with jazz legends like Charlie Haden, Elvin Jones, Paul Motian, and Jack DeJohnette—he began to take his talent seriously. “I was pretty adamant growing up that I wasn’t going to be a professional musician,” Redman says.

“Then all of a sudden I turned around and it was like ‘Bam!’ Within the first eight months in New York, I played with some of the greatest jazz musicians in the world  …  I’m not a religious man, but these were my gods.”

Redman’s blue-green eyes shine when he speaks about living the musician’s life for the first time and reconnecting with his father. Getting—literally—blown away by his dad on stage was the best music education he could ask for. “To have to solo after him night after night and just get my ass kicked, that was intimidating,” he says. When fans started asking why he went by his mother’s name of Shedroff, he told his dad to introduce him onstage as Joshua Redman.

It wasn’t long before Redman’s fame eclipsed his father’s. His first album, Joshua Redman, earned him a Grammy nomination. Newsday’s Gene Seymour called the record “simply the most startlingly assured debut album by a young jazz artist in memory.” On seven albums over the next nine years, he was consistently touted as one of the few fresh faces in jazz.

The 1990s were an interesting time in the New York jazz scene. The “young lions” era—a name marketers coined in the ’80s for revivalists like Wynton Marsalis—was waning and a more open approach to jazz was moving in. Redman’s innovative and eclectic sound filled the void nicely. (The standard “Body and Soul” and James Brown’s “I Got You (I Feel Good)” appear back to back on his first album.) Along with contemporary masters like Brian Blade, Nicholas Payton, James Carter, Brad Mehldau, and Kevin Hays, it seemed Redman was at the forefront of a renaissance—one that distanced itself from the ideology of what jazz should or shouldn’t be. “When I came to New York, people were trying to set up this dualism between traditional jazz and innovation. I think that’s not really there anymore,” he says. “We all immersed ourselves and have a great respect for tradition. But it’s not tradition with a capital T  …  I don’t think we’re trying to recreate or bring back something from the past. We all love jazz, but we all are very influenced by music other than jazz. I think there’s a real fluidity and a healthy eclecticism that exists in a lot of serious jazz musicians of my generation.”

All the clichés about becoming a father hold true. All those existentialist questions are answered. Life is not absurd anymore, you know? There’s meaning. This is why I’m here."

Redman lists more of his influences as we stroll past the 1930s Jazz at Pearl’s club: his father, Led Zeppelin, Ornette Coleman, and Stevie Wonder. He says his diverse taste synched well with the direction SFJAZZ (San Francisco Jazz) was headed in when they approached him in the late ’90s. Redman was tapped in 2000 to direct the West Coast’s answer to Marsalis’ relatively conservative Jazz at Lincoln Center. He helped foster progressive jazz by promoting an avant-garde repertoire, and collaborating with cutting-edge composers and players in the SFJAZZ Collective. He says he’s taking a break from the job this year, however. His life has changed drastically since he and his fiancée, Jennifer, had their one-year-old son, Jadon. They live just a block from where Redman grew up, and he tries to wake up with the baby when he’s not touring. (Jennifer might dispute this, he concedes.) “All the clichés about becoming a father hold true,” he says, grinning. “All those existentialist questions are answered. Life is not absurd anymore, you know? There’s meaning. This is why I’m here.”

We cross Columbus Avenue and Redman pauses to chat with two young musicians outside Lawrence Ferlinghetti’s City Lights bookstore. He’s gracious and curious while the pair discuss an album they just finished. When they leave I point out a collection of posters for Bukowski and Ginsberg readings hanging in the bookstore window. We discuss how the awesome talent that drove the two movements in the 1950s—Beat and bop—left generations of artists that followed in a kind of stasis. Even with the current renaissance in jazz, opportunities for musicians continue to dwindle, Redman says. (Warner Brothers dropped its jazz label several years ago and shuttled some jazz musicians to its subsidiary Nonesuch Records.) There are too many genres to compete with and listeners don’t have the time or patience for jazz. Then Redman laughs at how many of his musician friends are infatuated with American Idol.

Light is fading on the Transamerica Pyramid as we climb the skinny staircase in Vesuvio to get a last drink. The bar where Kerouac famously blew off Henry Miller to booze with his friends is quiet with just a  few  old-timers huddled near the taps. Redman sits by a window and orders a mineral water. Will the new album predicate a move back east? He’s not sure, he says. Right now he just wants to play.

He’s hesitant to say it, but it’s obvious that while recording Back East he hit on something—something he’s been searching for since he became a professional musician 16 years ago. “I am at a point now where I’m starting to learn how to play,” he says. “I feel confident that I may have my own voice and my own sound. I think it’s overwhelming out there, the music I needed to listen to and learn from and study, but now I feel like I have more identity. I feel like there may be something out there on the horizon.”