Maria Friedman With Theo Jamieson
‘Legacy’
Cafe Carlyle
Through September 28

By what standard is Paul McCartney’s “Blackbird” considered a simple song? True, on its surface there’s an easy-to-remember, nursery rhyme-like, sing-song melody, but both the words and the music are full of implications and interpretations. Mr. McCartney has told us that the harmony was inspired by Johann Sebastian Bach, and it’s also said that the lyrics are a thinly disguised statement about the civil rights movement in America.

To make “Blackbird” seem relatively simple is a matter of context: When Maria Friedman sang this Beatles standard roughly 30 minutes into her one-woman show at the Carlyle, it only sounded uncomplicated compared to what had come before it.  

An English actress, singer, and lately — and most famously — a director, Ms. Friedman has been associated with Stephen Sondheim for her entire career. In 1990, she played the leading lady, Dot, in the original London production of “Sunday in the Park with George,” and since then also appeared in “Passion,” and “Sweeney Todd.” More importantly, as a director, Ms. Friedman is generally credited with the more recent success of “Merrily We Roll Along,” a work originally considered a flop but that, thanks largely to her direction, now is regarded as a Sondheim classic.

It was Sondheim himself who put together Ms. Friedman’s first one-woman show at the Cafe Carlyle 20 years ago, and now she both begins and ends her latest offering, “Legacy,” with his songs. 

Ms. Friedman starts, paradoxically, with “Being Alive,” the ending song of “Company.” She then tells the improbable but true story of her first major brush with Sondheim’s music, when she, to everyone’s surprise and especially her own, was asked to perform “Broadway Baby” at an all-star, all-Sondeim Drury Lane benefit concert about 40 years ago. She says she found her original motivation to sing that “Follies” standard because the words fully captured her own story — that of a young, inexperienced but determined musical theater hopeful. Singing it now, she not only projects herself into the character, but moves backward into her younger self.

At this point, we reach the main event of the evening: a highly ambitious construct she calls “Sunday in the Park with Dot.” Lasting nearly 15 minutes, this is essentially a compact but complex reworking of the 1984 score; she reconstructs the work as a one-hander, telling the story entirely from Dot’s point of view. You might say that she has transformed “Sunday in the Park” into the format of “Yentl,” a fully realized work of musical theater that focuses on a single leading character who sings all the songs.  

Ms. Friedman moves from the title song — in which Dot ruminates to herself the highs and lows of dating an enormously talented but equally obsessive and diffident artist like George —  to “Everybody Loves Louis,” “Children and Art,” “We Do Not Belong Together,” and eventually to “Move On.” Somehow Dot and George get two farewell songs, one for each act. 

Along the way, she lingers on “Finishing the Hat.” This is famously sung in the actual score by George, but Ms. Friedman illustrates how this most characteristic of Sondheim anthems — he used the title for his first book-length collection of his lyrics — suits Dot just as well.

After this multilayered montage of some of the more complicated songs from Sondheim’s most adventurous work, anything would seem relatively simple. This is why “Blackbird” is so welcome at this point: Mr. McCartney’s song is at least straightforward and sincere. 

She next shifts gears once again, into Randy Newman’s arch and ironic — even perverse — “Short People,” explaining that she extended to a close friend the chance to submit one request and this was his favorite song in the world. Here, the expert accompanist Theo Jamieson, who looks, through these American eyes at least, exactly like the P.G. Wodehouse character Bertie Wooster, joins her in harmony. 

She restores Mr. Newman’s credibility with his more compassionate “When She Loved Me.” She also recounts her long relationships with both the late Marvin Hamlisch, with “Nothing” from “A Chorus Line,” and with Andrew Lloyd Webber, with “Any Dream Will Do” from “Joseph and the Amazing Technicolor Dreamcoat.” This non-Sondheim interlude also includes Joni Mitchell’s “Both Sides Now” and, fittingly, “A Piece of Sky,” from “Yentl.” 

The third act, as it were, of the 80-minute show brings us back to Sondheim, with “Losing My Mind” and “Somewhere.” In between the two she sings “Send in the Clowns,” taking the famous Sarah Vaughan interpretation as a template: Here, it’s less an aria than a secular prayer. 

On a larger level, nearly all of these songs, Sondheim and otherwise, draw their dramatic power from the distinction between dreams and reality, or between expectations and actuality. She succeeds on both of these levels, and a lot more besides.