The surprise off-Broadway hit of the 1959–60 session was a drama with music in which both halves of the equation — the play, the music, and the way they complemented each other — were completely unlike any other production before or since. This was “The Connection,” a wildly successful, avantgarde theater piece that eventually led to an equally far-out experimental film, two all-time classic jazz albums, and, this Monday, a concert at Merkin Hall featuring the original music as played by the original composer-performer, the pianist Freddie Redd.

In 1959, “The Connection” was the brainchild of Jack Gelber, an aspiring playwright who had the brilliant idea of concocting a unique theatrical experience around the idea of drugs and jazz. But rather than stage a traditional narrative on a theme of addiction and redemption, as had been done before (most famously in the bestselling novel and film “The Man With the Golden Arm”), Gelber had the innovative idea of creating a play in what he regarded as a “jazz style,” in which actors played characters who continually interacted with the audience as well as with each other.

There was a plot — a bunch of junkies wait around in an apartment for their connection to show up, as if he were Godot or the Iceman — but the most important facet was the “solo”-like fashion in which each character got up, one by one, and seemingly improvised an entire philosophy. The four main characters commented and riffed on each other like a bassist and a drummer trading fours. Much of the dialogue was carefully worked out, but other moments were spontaneous. When the jazz critic Ira Gitler attended a performance, the actors buzzed about a famous reviewer being in the house. Everything about the play was radical: the subject matter, the way black and white actors interacted as equals, the use of four-letter words, and the acknowledgement of other taboo topics (“Leach is a queer without being a queer — he even thinks like a chick!”).

Of the four primary performers, one, Gary Goodrow, had also played tenor saxophone professionally, and another was an actor playing a musician who was incapacitated because he had hocked his horn to buy junk. Mr. Redd came into the picture at the recommendation of Mr. Goodrow, who was a friend and Lower East Side neighbor. At the time, Mr. Redd had played all over the jazz and rhythm-and-blues scene and recorded several albums for the Prestige and Riverside labels. Mr. Goodrow introduced him to Gelber, whose original idea was to have a jazz group on stage playing standards and familiar tunes.

Mr. Redd came with two brilliant ideas. First, as he recalled in a 1988 interview, “I told [Gelber] that I wanted to write an original score. He said, ‘Hey listen, if you can write this music, fine, you’ve got it.’ I went home and I started writing. I did the play for 17 months.”

Second, he brought his old friend from his native Harlem, the great bebop alto saxophonist Jackie McLean. Unlike Mr. Redd, who had never experimented with anything harder than marijuana, McLean was slowly weening himself from a long heroin habit; the show proved a lifeline for both men, who were unable to work in jazz clubs at the time due to previous violations of the cabaret code. McLean’s presence also attracted the attention of Blue Note Records, which recorded the score in 1960, as well as two additional albums by Mr. Redd. (There even was a “cover” album of “Music From the Connection” by the trumpeter Howard McGhee on the Felsted label, featuring Mr. Redd under a pseudonym and the tenor saxist Tina Brooks replacing McLean.)

Another of Mr. Redd’s innovations was to score the production with bright, even cheerful modern jazz; almost anyone else would have tried to come up with something dark, heavy, and melodramatic (as Elmer Bernstein did in his famous film score to “Golden Arm”). Even though most of the seven selections Mr. Redd wrote for “The Connection” are in minor keys, graced by McLean’s distinctive intonation, this is upbeat, joyous music: “Sister Salvation” is one of the few marchtempo jazz tunes to pick up the gauntlet thrown down by Benny Golson’s “Blues March”; “Music Forever” is a memorable melody equally inspired by “My Shining Hour” and “Sleep.” Even “O.D.,” which accompanies the climactic scene, in which the “Leach” character is given an extra dose of junk and nearly dies, is far more peppy than morbid. Still, as Mr. Gitler, who annotated the original album, pointed out to me recently, “There is often an underlying angst mixed in with an undeniable romanticism.” That’s why Mr. Redd’s marvelous music still makes all of the emotional connections it did back in 1959.

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This being Valentine’s week, there is no shortage of outstanding singers in the city, from one-night stands by Janis Siegel and Tierney Sutton (how romantic is that?) to longer runs by Vanessa Rubin (with Victor Goines at Dizzy’s); Ernestine Anderson (Jazz Standard); the Queen of Birdland, Hilary Kole; and His Royal Hipness, Kurt Elling, at the Blue Note. Yet no act is more worth hearing than the amazing mother-and-son duo of Sandy Stewart and Bill Charlap, who have just begun a two-week run at the Oak Room.

I’ve always thought that cabaret is the most intimate of performing arts, yet Ms. Stewart and Mr. Charlap create such an incredibly intimate bond with both the audience and each other that they make even most of the other Algonquin performers look like exaggerated extroverts by comparison. The Oak Room is the epicenter of the deepcontext cabaret of Andrea Marcovicci, Mary Cleere Haran, and Maude Maggart, for whom the singing is only part of the show. By decontextualizing the music — Ms. Stewart barely introduces her son, let alone the songs — the two vanquish any idea of a barrier between performers and crowd. There’s nothing to fall back on, no place to hide. She knows that she doesn’t need any such safety net (or even a bass and drums), since the more of her we can hear, the more we realize that both her intonation and interpretation are as close to perfect as is humanly possible.

My personal highlight of the quickly moving hourlong show was Arthur Schwartz’s “I See Your Face Before Me.” Elsewhere in the program, Mr. Charlap alluded to Art Tatum when he began with a faint echo of Bill Evans’s “Peace Piece.” Ms. Stewart vividly animated the idea expressed in Howard Dietz’s lyric, that the object of love can become a recurring theme in a person’s head, like a piece of music. She sang it so believably that everyone in the place could see faces of lovers past and present hanging in front of them.

wfriedwald@nysun.com