In the subgenre of small-scale bio-shows of legendary musical performers, "Lady Day at Emerson's Bar and Grill" has been a popular attraction, not just re-creating the songs of jazz singer Billie Holiday but offering a poignant dramatic structure that plays like one of her own sad and haunting songs.

In the subgenre of small-scale bio-shows of legendary musical performers, “Lady Day at Emerson’s Bar and Grill” has been a popular attraction, not just re-creating the songs of jazz singer Billie Holiday but offering a poignant dramatic structure that plays like one of her own sad and haunting songs. The work has long been a staple of small and regional theaters since Lonette McKee bowed with it Off Broadway, giving a variety of actresses a chance to place gardenias in their hair to conjure a lonely, lost artist near the end of the line.

In the Long Wharf production, two-time Tony nominee Ernestine Jackson (“Raisin,” the black revival of “Guys and Dolls”) presents the singer as a simultaneously strong and desperate figure who finds some solace in her songs, but more in her own personal “moonlight” of drugs, booze and memories. Jackson nicely suggests rather than mimics the famous Holiday deeply lived sound in a show filled with more than a dozen tunes accompanied by an accomplished trio.

But this is far from a simple songbook, and the cumulative power comes in the unraveling of an addicted artist and her story at the end of her days. Jackson is solid, sometimes too solid, in the role, lacking sufficient vulnerability and fragility to build to her tragic end. She is not helped by Lonny Price’s unfussy but not always clear direction.

Show is set in a small bar in South Philadelphia where Holiday performed four months before her death in 1959 of cirrhosis and heart failure at 44. The return to her old stomping grounds not for nostalgic reasons but out of necessity sets the scene for this last-chance gig before she finally gives up the ghost for good.

Though she’s there to sing, it is clear that Holiday has more than music on her mind. In her own entertaining no-nonsense, chatty style, she is profane, headstrong and often funny as she recounts the highs and lows of her life and career to the audience. Pianist and intended husband Jimmy Powers (Darryl G. Ivey) tries his best to keep the singer on the musical track, but as her stories meander and darken, it’s clear where she is headed.

She talks about her adored mother, her musical father and her poverty-stricken childhood in Baltimore. There are musical influences Louis Armstrong and Bessie Smith. (Jackson does a fine Smith tribute, “Pigfoot,” blending the best of two great artists.) There are also anecdotes of performing with the Artie Shaw band in the Jim Crow South and at Carnegie Hall and of her problems with the city of brotherly love. (“Philly’s been the rat’s ass for me,” she says.)

Her despair deepens as she talks increasingly about her first husband, Sonny (“my first love and my worst love”), who introduced her to an unshakeable heroin addiction, and her ongoing experiences with racism and the law. But Lanie Roberts’ script does not fully comes to terms with Holiday’s many contradictions. Too often, it veers more than builds.

“God Bless the Child,” “Foolin’ Myself,” “Crazy He Calls Me,” “What a Little Moonlight Can Do” and the powerful “Strange Fruit” are performed at strategic intervals, and Jackson handles the gliding jazz minimalism beautifully. She makes Holiday’s fleeting happiness a joy and her suffering an art.

In the intimate thrust space, James Noone creates a suitable nightclub environment that’s given a bit of glam depth with a mirrored backdrop. (The blood-red painted empty tables, chairs and wine bottles downstage are a few symbols too many, however.) Rear projections of central figures in Holiday’s life help illustrate the autobiography and offer a collective payoff at the end. Robert Wierzel’s smoky lighting and Tracy Christensen’s luminous ’50s ivory gown also are right touches.

Lady Day at Emerson's Bar and Grill

Long Wharf Theater, New Haven, Conn.; 487 seats; $60 top

Production

A Long Wharf Theater presentation of a play with music in one act by Lanie Robertson. Directed by Lonny Price. Music director, Darryl G. Ivey.

Creative

Sets, James Noone; costumes, Tracy Christensen; lighting, Robert Wierzel; sound, David Stephen Baler; production stage manager, Laura Skonik. Opened, reviewed Nov. 2, 2005. Runs through Nov. 20. Running time: 1 HOUR 30 MIN.

Cast

Billie Holiday - Ernestine Jackson Jimmy Powers - Darryl G. Ivey
Musicians: Phil Bowler and Jesse Hameen II.

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