'Young people take note of this woman's life, this woman's bravery, so you can stand up and not be afraid to speak in your own voice. Children, stand tall and dare to be a Billie Holiday."

Dee Dee Bridgewater Universal

So writes singer Dee Dee Bridgewater in a note to her latest CD, "Eleanora Fagan (1915-1959): To Billie With Love From Dee Dee" (DDB Records/Emarcy), a tribute whose title begins with Holiday's given name. Ms. Bridgewater has considerable experience with daring to be a Billie Holiday, much of it literal. She earned critical acclaim in Paris in 1986 and a Laurence Olivier Award nomination the following year in London for her portrayal of Holiday in Stephen Stahl's play "Lady Day."

"I was possessed," she said. "I would take my first step onto the stage and could feel her take over." Ms. Bridgewater can do a dead-on impersonation of Holiday—she briefly eased in and out of Holiday's drawn-out phrasing and playful intonation over the phone for me—but that was never the point.

Holiday's story, not her singing, first captivated Ms. Bridgewater. "When I was a teenager, I believed that to be a jazz singer you had to scat and sing like Ella Fitzgerald or Betty Carter," she said, "and you needed to have range. We all know that Billie did not have an extensive vocal range."

But Ms. Bridgewater had read "Lady Sings the Blues," Holiday's 1956 autobiography, co-written with William Dufty, on which Mr. Stahl's play was based. "I was struck by a lot of things that I could relate to or had experienced, including abuse," she said. "And I began to understand how she ended up growing into the person she grew into, what her singing meant."

By the time she was cast as Holiday, Ms. Bridgewater had developed a deepened appreciation of Holiday's rhythmic and expressive gifts as a singer. And she sought something beyond the tragic storyline. She had easy access to good sources: She'd debuted in 1970 with the Thad Jones/Mel Lewis band, which included her then-husband Cecil Bridgewater, and performed throughout that decade with jazz standard-bearers including Max Roach and Sonny Rollins. Through musicians such as trumpeter Harry "Sweets" Edison, she heard firsthand recollections. She acquired cassettes documenting private moments. "I learned that Billie was a very funny woman, with a dry sense of humor," she recalled, "who loved to talk dirty and would cook for her fellow musicians."

Now, at 59, the prospect of a Broadway revival of Mr. Stahl's play prompted Ms. Bridgewater to envision a two-disc set: one evoking the play's era, the late 1950s; the other a celebratory tribute in the here-and-now. When the recession put the play on hold, she scaled down to the latter idea. The result sounds bold, varied, modern and complete.

Ms. Bridgewater's performance style is often wildly extroverted, spanning a broad emotional and musical range; it is in many ways the polar opposite of Holiday's finely focused presence and introverted demeanor. On the new CD, though Ms. Bridgewater flecks a lyric or two with Holiday's timbre or phrasing, her singing is never imitative, often reflective of musical liberties Holiday never took.

Tune In

Listen to clips from Dee Dee Bridgewater's new CD, "Eleanora Fagan (1915-1959): To Billie With Love From Dee Dee."

"I wanted to capture Billie's spirit," she said, "as channeled through the woman and the musician I am today." She turned first to pianist Edsel Gomez, with whom she has worked for seven years, and then enlisted bassist Christian McBride, drummer Lewis Nash, and James Carter, who excels equally on a variety of reed instruments. She asked Mr. Gomez to create musical contexts for 12 songs strongly associated with Holiday, more loose-limbed musical frameworks than tight arrangements.

The pentatonic piano figures—meant to evoke an African balafon—and swift 6/8 rhythm of the opening track, "Lady Sings the Blues," sound less like an homage to Holiday's music than an extension of Ms. Bridgewater's previous CD, "Red Earth," for which the singer immersed herself in the musical traditions of Mali. There, Ms. Bridgewater forged a deep connection with Sékou "Bassékou" Kouyaté, a master of the ngoni, the narrow lute popular throughout West Africa.

On the new CD, Ms. Bridgewater seeks—and finds—a similar bond with Mr. Carter, recalling in some small way as well the storied communion between Holiday and tenor saxophonist Lester "Prez" Young. Mr. Carter's pithy soprano saxophone improvisations urge on her scat-singing during "All of Me"; his choked-up bass-clarinet utterances punctuate her tearful ending to "Strange Fruit."

"Honestly, there aren't too many vocalists around these days who you can genuinely feel, who allow themselves to be felt," said Mr. Carter. "That's what was at the core of Billie's relationship with Prez: no inhibitions about playing with each other and really making a connection; finishing one's phrases, invoking another's thoughts about a lyric. With Dee Dee, it's possible."

Ms. Bridgewater conjures maudlin echoes of Holiday's persona here and there (perhaps a bit too literally on "Strange Fruit," just right on "You've Changed") but more often provides an alternative narrative through songs Holiday favored. Often, there's joyful abandon ("Nash it to me," Ms. Bridgewater exclaims during a solo to "Miss Brown to You"). "I refuse to look at Billie as just a tragic figure," she said; her album, in effect, sees a drug-addled life cut short through the eyes of a survivor at the height of her powers. "This recording is me and the band, doing what we do best," she said. "And if Billie was in the room, her presence was light, subtly telling us what to do."

Indeed. Mr. Gomez had transposed "Lover Man," a tune indelibly linked to Holiday, to the key of E for a fresh approach. Upon playback, it didn't sound right. He and Ms. Bridgewater tried out F, toyed with D. The version we hear is back in the original key, C, the way Holiday heard it.

Mr. Blumenfeld writes about jazz for the Journal.