The cover of singer Cassandra Wilson’s new album, Silver Pony released today on Blue Note Records, features a drawing of a young Wilson in cowgirl duds on a horse. The illustration is based on a photo taken of the singer when she was just a toddler. And though the young Wilson looks tiny up on the horse, she doesn’t appear to be clenching the reins or exhibiting any fear. “Quite the opposite,” she says, chuckling. “I’m not holding on for dear life. It’s strange. I don’t remember my feelings then, but I know that I’d not been around a lot of horses. I’d seen horses. I’d gone to the fair to see them. But it looks as if I’m really relaxed and confident.” Indeed, her pose in the portrait seems an appropriate foreshadowing of her own future as an artist, confident and determined in her own creative direction.

Wilson recalls the day it was shot as if it were yesterday. “That was a pony that was brought around in the neighborhood for kids to take pictures with. I was a little tot-four and some change. My mother asked the guy to come for my brother, not for me. I was just looking at the pony, and thinking, ‘Why can’t I take a picture with the pony?’ She [her mother] didn’t really think that was a good idea, because I was a girl, I guess. But it turned out that I was the only one who took advantage of that pony ‘op.’ It’s a cherished photograph. The look on my face is so furious. I look at that picture often and I try to remember what was on my mind and why I was so furious. Kids usually smile. They’re usually smiling or giggling or laughing. But I was so serious. I think I believed I was a cowgirl!”

The ersatz cowgirl eventually grew up to become one of the most important and influential jazz singers of her generation. Born and raised in Mississippi, Wilson moved to New York City in the early ’80s and fell in with a loose coalition of creative types based mostly in Brooklyn, who named themselves M-Base Collective. Saxophonist Steve Coleman, one of the group’s most active and outspoken members, became an early mentor of sorts to Wilson who was already well on her way to finding her own voice. Wilson released a series of critically-acclaimed albums for Stefan Winter’s JMT label, including Blue Skies, Jumpworld and She Who Weeps. In the early ’90s, Wilson signed with Blue Note and proceeded to release a series of albums, initially produced by Craig Street, that changed the game for jazz vocalists, thanks in part to non-traditional instrumentation and repertoire and in part to Wilson’s expressive voice and individualistic phrasing. She’s also recorded plenty of mainstream jazz with artists such as Wynton Marsalis and Jacky Terrasson. And her very personalized take on Miles Davis’ music, Traveling Miles neatly showcased her ability to transform any material into her own.

Wilson’s new album itself is a different kind of hybrid, with most of the tracks recorded live in performance and few done in the studio. Wilson had not recorded a live album in a long time and she says that she simply liked what she heard from her group. “It was time to do a live album, or something like a live album,” she explains. “It was the perfect opportunity with this band. I thought I was going in to do a studio album, but I started listening to some of the tapes of the tour we’d done in 2009. A lot of the music was really compelling with good quality recordings.” Although the live recordings weren’t done originally in multi-track format, Wilson was able to lean on engineer and co-producer John Fishbeck to make it work. “This guy is really special,” Wilson says. “He’s got some serious toys.”

Wilson’s band-Marvin Sewell on guitars, Jonathon Batiste on piano, Reginald Veal on bass and Herlin Riley on drums-is the type of jazz group who can play nearly any kind of music, from folk to blues to R&B and even swinging jazz. A few of them have played with her off and on for a long time, while others are newer to the fold. She says that the group has come together as a result of their affinity for her musical approach, as well as because of her respect for their mastery. “It’s evolved beautifully, the way it should. If you stay in this business long enough, you get to the point where you attract certain kinds of musicians. I feel really blessed that I can share the stage with talent like this.” A key voice in the group is guitarist Marvin Sewell who has been playing with Wilson for many years. “The first album he did with me was Traveling Miles. He and I are a couple, musically. He plays the guitar the way I would play it, if I could play well. He also mirrors what I’m doing vocally and he takes it to another level. I look at Marvin as a cross between Muddy Waters and Wayne Shorter.”

Her rhythm section of Veal and Riley has played together for a long time even before working with Wilson, most notably in the bands of Wynton and Branford Marsalis. “Yes, they’re a matched pair. They have a shared language. They have been working together on and off in various configurations for over 20 years.” And the pianist Jonathon Batiste is truly the “kid” in the band. “We call him the young master,” she says. “He too shares a style and language with Herlin and Reginald. There you have a little clique.” Indeed, it is like a separate jazz trio within her group, with Sewell adding an entirely different sonic color. “There’s a history of that in the music. Unless you play a real fat round sounding guitar, historically, you’re not invited to join in to the festivities.”

Orrin Keepnews said he used to try to keep Bill Evans in the dark about which set they were recording because he didn’t want him freezing up in some way. Wilson says that she was concerned that her band would bring the same energy to the live recording that she heard on the tapes. But she didn’t keep them in the dark about the recording. “I wanted the guys to expand what they had done on tour. So I played them excerpts from the performances, especially when I heard them do something interesting. They have a lot of freedom. When we’re performing a live show, I usually give them five to ten minutes to loosen up and to establish a groove and to go some place if they want to go some place musically. There are portions of the live performance that I played for them and I said to them, I want you guys to go in there and get back into the same head space. Listen to the music and go there.”

Over the years, Wilson has created some real masterpieces in the studio: From Blue Light Til Dawn and New Moon Daughter through Traveling Miles and Loverly. This is no accident. It seems that Wilson counts herself as one of those artists who doesn’t just “knock out” an album every year, but rather hopes to craft something special. “It matters a lot to me. It’s more than documentation between tours. It’s an offering. I want it to stand up and I want it to mean something to me. That’s why they don’t come as often perhaps as people would like. But there’s a lot of work, thought and love that I bring to anything that I want to share with an audience.”

This particular recording features a few high-powered guests, including John Legend and Ravi Coltrane. Wilson duets with Legend on “Silver Moon” a song co-written by the pop singer-songwriter. “We played a concert together in Florida, as part of Jazz in the Gardens. Our ‘people’ met each other. Then later his people contacted my people and said that he had a song for me. When we met, he said that he was a fan and that he knew every song on New Moon Daughter. I was really shocked, but not too shocked because when I first heard his song and I was listening to his approach and voice, and I heard a little something that reminded me of me. It worked out so beautifully. He was very humble and sweet. It was great working with him.”

Given Wilson’s sumptuous voice and demonstrably catholic tastes in music, you’d think she might think about going for the gold and making a purely pop crossover record. She doesn’t go for that sort of second-guessing though, as much because she’s never seen herself as the compromising sort. “I don’t really believe that I ever felt that that kind of music was for me, because I’ve always had a real adventurous spirit. It was always difficult for me to color inside the lines. I would take my crayons and create little figures outside the lines. I never passed that litmus test that pop singers have to have-that ability to stay within a form and formula that is acceptable a broad swath of the population. I never thought that was possible. But I always thought I would love to write pop music and songs for other people.”

In fact, Wilson is a talented, if not terribly prolific composer. She last wrote a lot for a record back in 2003 with Glamoured. She has just two songs on Silver Pony, and she shares the credit for those with much of her band. It seems that writing songs requires one thing she often has way too little of. “Time. Just having the time to myself. I’m discovering that now, what is it that gets the song out, because I don’t write the way I used to. And I would really like to get back to that. I enjoy writing. The great songs come from inside you. I try to write something every day. Even if it’s just a snippet of something, I try to challenge myself with something every day. But they’re just fragments. Sometimes I go back to them and listen to them again and say, ‘Wow, I could make something out of that.’ And sometimes they just remain fragments.”

Wilson has become famous in the jazz community for using material from relatively non-typical writers (Joni Mitchell, Neil Young, old blues, Hank Williams, etc.), many from well outside the usual jazz standards lexicon. In a recent interview with Jane Monheit, she credited Wilson with opening the door for contemporary jazz singers to look beyond the Great American Songbook. Wilson says she looks for a personal connection when choosing material. “I know it’s right if it resonates and if the story that I’m singing about has a very specific meaning to me. Those are the songs that keep popping up in your consciousness if you have some sort of connection with them. It’s usually at some deep emotional level. It’s either your story or it’s a story that you remember.”

In the wake of Wilson’s great records, particularly the early ones on Blue Note with Craig Street producing, we see so many singers somehow in her shadow for better or worse. It’s hard to imagine artists like Norah Jones, Madeleine Peyroux, Melody Gardot or Lizz Wright reaching wide audiences they have without the groundwork laid by Wilson and her organic approach to jazz vocals. I wondered if she heard herself in all those rootsy and folksy jazz singers that are out there. “Yes, I do sometimes. It sounds great. It’s really rewarding. I love it. It means that I’m doing something right. And that the younger singers that are coming along are paying attention.”

When Wilson first came onto the scene, during her early days based in Brooklyn and collaborating with Steve Coleman and the M-Base artists, she was frequently compared to Betty Carter, perhaps because she was neither a typical torch singer nor a jazz scatter. Back in 1990, the critic Leonard Feather wrote a somewhat grudging review in JazzTimes of Wilson in which he observed that Wilson had always been called the next Betty Carter, but that it sounded like she finally had become the first Cassandra Wilson. But really, no one truly sounds like Betty Carter, a complete original in nearly every way. And the same could be said for Wilson, even acknowledging those younger singers who have incorporated some aspects of her approach into their own. I asked Wilson how she sees her own voice and music as changing or developing over the years. “I feel as if it’s anchored, yet it still has an exploratory side to it. It’s broader. The texture of it seems to have grown stronger. I really enjoy listening to my voice now. I didn’t when I first started out. I didn’t like the sound of my voice. I always thought there was something else hiding there. It seems as if what was hidden has come out.”

In the last ten years or so, Wilson has spent a lot of time in Jackson Mississippi, her hometown, in order to be close to her mother and family. She says that she has always had a strong connection to Mississippi and her roots have always been deep there. “When I went back, I did have an opportunity to come to terms with that [her personal and musical roots] and to spend time with community, family and friends. It was wonderful but I’m back in New York again. I’m going back and forth. And I have a place in New Orleans as well.”

Wilson has been recording with Blue Note for over 15 years and became one of that label’s cornerstone artists, but now we’re seeing the major labels experiencing real difficulty. Yet Wilson is sanguine about her future with the label. “I don’t think it’s having any impact on artists like me. I’m fortunate in that my relationship with Blue Note could go on forever. I think they’re going to be around for a long time. I don’t know, I just get that feeling. If they continue to take the kind of care that they take. If they continue to keep putting out the same kind of highly evolved music, they’re going to be okay. As for the pop industry, I don’t know about that. Record companies had grown to be sort of monstrous and out of touch with artists and so maybe this is a way of leveling things, this whole cycle we’re going through.”

Wilson says that the future is wide open as far as her next recording. She’s not one to line up her projects way in advance, but rather prefers that they evolve organically. “I’m going to tour for this record and, as I often do, see what happens. You go out to do live performances and then new music surfaces and new ideas happen as a result. You can’t stop and say, ‘Oh, I’m going to get out of this and do something else.’ You have to see this through to the end. See where this takes us. How far can we go with this?.How much further can we develop this music? It’s a long process. Sometimes it can take up to a couple of years before you get to the next point. Or it can take a year. You can be in it and then great, we’ve come to the end and the new material has appeared. Let’s go back into the studio and do something.”

Wilson has been producing herself off and on for many years and has evolved into a highly skilled producer. It would seem that the next step would be for her to produce other artists. “There’s only one artist I’ve produced and that’s Rhonda Richmond on my own label, Ojah Media Group. I’ve done two of her recordings. I would love to produce more and I would love to share what I’ve learned with other artists, younger artists. That would be great to have that opportunity. And to have the time to do that. We’ll see what happens.”

Regardless, Wilson is very clear about her mantra for her own development as a creative artist. “I keep learning. I keep evolving.”