Landing tickets to see jazz legend Billie Holiday sing live is the kind of dream that long ago got tossed into the same “dead ambitions” bin as “marrying James Dean” and “becoming the fifth Beatle (or at least a Bee Gee)” — all decades past the realm of possibility. But this weekend at the Yale Cabaret’s season opener, “Lady Day at Emerson’s Bar and Grill” manages to bring at least one dead dream back with the same flawless grace and captivating poignancy that Ms. Holiday herself was so famous for.

Written by playwright Lanie Robertson and directed by Patricia McGregor DRA ’09, “Lady Day” sets the stage during one of the last performances of Billie Holiday’s career. It takes no stretch of the imagination for the Cabaret’s intimate size and setup to become a small Philadelphia nightclub; and it is in the closeness of this setting that Lady Day — played by Christina Acosta DRA ’10 and, on Saturday night at 8 p.m., by Emily Jenda ’10 — both performs and recounts some of the most memorable moments of her life and career with the casual ease and familiarity of an old friend. Charismatic, sincere and captivating, Billie flaunts the stories of her successes, heartaches, mistakes and dreams.

The audience, lounging in the Cabaret’s café-style tables and chairs, becomes as integral a part of the play as Billie and her microphone. Billie often saunters over and directly addresses her fans, taking sips of their beer or, as in one instance, playfully pointing out the color of their socks. Direct eye contact made while singing furthers the already convincing impression that it’s the real Billie Holiday standing and baring her soul right in front of you.

Musical as well as dramatic and entertaining, “Lady Day” features many of Billie Holiday’s most famous songs, including “What a Little Moonlight Can Do,” “God Bless the Child,” “Ain’t Nobody’s Business If I Do” and “Where Our Love Has Gone.” The songs are performed at key moments throughout the play to appropriately reinforce the wide range of emotions and thoughts through which Billie so deftly leads her audience. Accompanied on piano by the only other actor in the play — Aaron Moss DRA ’10 in the role of Billie’s fiancé and accompanist, Jimmy Powers — Holiday’s tunes are performed with an accurate, jazzy soulfulness that at times makes the music seem almost like a third character. Open-palmed and stroking at the air, Billie sings the first tune of the play, “I’m Yours,” almost as if she is physically caressing it. A few minutes later, it turns out that Billie sees herself exactly that way. “I gotta sing the way I feel. I gotta roam around and find the song,” she declares, hands flowing through the air. And Jimmy, though evidently a prominent person in Billie’s life, speaks only a few lines throughout the otherwise one-woman show; he is heard almost exclusively through the notes of his piano.

Sad, charming, funny and inspiring, not to mention filled with infectious, superbly performed jazz beats, “Lady Day at Emerson’s Bar and Grill” makes for an extremely promising start for the Cabaret’s new season. And although it is relatively short, with a total running time of only about an hour, “Lady Day” easily leaves you under the firm impression that you and the venerable Ms. Billie Holiday were BFFs in high school — with, you know, that whole death 50 years ago thing being a totally ignorable technicality.