The most recent opening night at the Crossroads Theater Company was memorable for two reasons: It was wonderful to see the theater, winner of the 1999 Tony Award for Outstanding Regional Theater, filled to capacity. The event was “Yesterdays: An Evening with Billie Holiday” starring Vanessa Rubin. One could say that the life of the late and legendary jazz singer was as fraught with ups and downs as was this theater.

It is heartening to see the theater enjoying a renewed future. Dedicated since 1979 to enriching and diversifying the representation of African-American culture, Crossroads had a financial setback in 2000 that forced its closing for two years. Since it reopened in 2002, it has been slowly and steadily rebuilding its support base. Sadly Holiday didn’t have the resources or the support base to help her survive. So it is also heartening to see that the Holiday legacy is attracting fine singers like Rubin who keep the Holiday canon alive.

Staged as a final gig in a nightclub in 1959 just two months before Holiday’s death at the Metropolitan Hospital in Manhattan, “Yesterdays” provides the appropriate setting for a glimpse at Holiday’s physical decline. However progressively intoxicated and drug-enslaved, Holiday was intent on sharing her talent until the bitter end.

In this her last public performance, she intersperses her repertoire with biographical digressions, many about her “mom” and her idols Louis Armstrong and Bessie Smith. Amusingly enacted, Rubin gets laughs for these diverting moments, including one in which she describes a family funeral run amok. She is backed up and on occasion held up by a terrific trio — Levi Barcourt (piano), David Jackson (bass), Bernard Davis (drums) — that has an opportunity to shine from the overture with a rousing version of (appropriately) “Lady Be Good.”

The structure of this musical play, as written by Reenie Upchurch and directed by Woodie King Jr., basically relies on Rubin’s ability to finesse her way from each song to a section devoted to animated narrative. However, there are also too many bumpy transitions for Rubin, who, while successfully capturing the essence of Holiday’s style, is deigned to sustain and magnify Holiday’s state of inebriation, later infused with heroin. It’s rather like an overdose for the audience.

Rubin rarely sings without a glass of whatever in her hand, sometimes clutching the microphone to steady herself. One can only admire Rubin’s efforts to create and sustain a character filled with remorse and rage as well as with the will and the need to share her principal gift. She lets us know she is aware of the narcotic agents standing at the back of the theater, waiting to take her away as soon as she stops singing.

Rubin looks terrific in a stunning white gown (credit to costume designer Ali Turns) and with Holiday’s signature white gardenias placed on the side of her sleek pulled back hair. What I appreciated most about Rubin, a New York-based jazz vocalist, composer, and lyricist, was the way she connects with the audience in a manner not unlike that of Bette Midler, as one observes the slightly ribald and ribbing I’ve-got-your-number insinuations that Rubin uses when picking out and flirting with a member of the audience, “Michael, I’m taking you back to Baltimore.”

Beginning with the obligatory “Good Morning, Heartache,” the mood is, indeed, heavy on the heartache. Rubin plunges deep into the sorrows of “Strange Fruit,” the plaintive “God Bless the Child,” the reflective “Yesterdays.” These are balanced by the bouncy “Them There Eyes,” and “Gimme a Pigfoot,” among 16 songs in all, one of which is performed winningly by drummer/vocalist Davis.

A trifle long at over two hours, “Yesterdays” is greatly enhanced by Antoinette Tynes’s lighting but less so by scenic designer Anthony Davison’s black back curtain. But who needed more than the embracing voice of Rubin to celebrate the memory of a musical icon?

“Yesterdays: An Evening with Billie Holiday,” through Sunday, February 27. Crossroads Theater Company, 7 Livingston Avenue, New Brunswick. $40 to $50. 732-545-8100.

Facebook Comments