New York’s spring cabaret and songbook season is divided between living legends and new stars, the traditional and the unexpected.

The discrepancy between veterans and younger headliners is exemplified by the March and April headliners at the Café Carlyle, who, as it happens, are two of the sexier women singing the Great American Songbook: Jane Monheit, who sounds especially good when she’s vocalizing in Portuguese and doesn’t have to worry about the lyrics, and the marvelous Keely Smith, who will be swinging her up-tempos, crooning ballads, and flirting with her band and the audience throughout April.

Staying with the songbook, the events I’m most looking forward to are the two City Center Encores! Productions — Irving Berlin’s “Face the Music” (March 29-April 1) and “Stairway to Paradise” an original revue of vintage revue material from the 1920s and ’30s. At Town Hall, “Broadway by the Year” has now joined the 92nd Street Y’s “Lyrics and Lyricists” as Gotham’s primary cabaret-concert series and will feature songs from the shows of 1938 (March 26) and 1959 (April 30). Meanwhile, the Y will honor the great lyricist Leo Robin (May 5–7) in a program hosted by Andrea Marcovicci, who will also do her customary Spring Fling at the Oak Room starting a week later.

The Algonquin remains ground zero for headliners in songbook programs: K.T. Sullivan and Mark Nadler will continue with their program of lyrics by Betty Comden and Adolf Green (through April 14), and will be followed by Karen Akers in a program by the composer Jule Styne (April 17-May 12). Considering that Comden, Green, and Styne wrote so many shows together, one can’t help but wonder if any songs will be duplicated. After Ms. Akers, the Oak Room will host two much-anticipated acts from England: the excellent jazz singer Claire Martin and the zany femme trio the Puppini Sisters.

At Feinstein’s, the emphasis is on the eclectic, from regulars and Broadway veterans Betty Buckley (March 27-April 7) and Linda Eder (May 1–12), to such wildcards as comic Jackie Mason (presumably not singing, but who knows? April 10–21) and ’70s pop idol Donny Osmond (April 24–28).

The new kid on the cabaret block is the Metropolitan Room, where the big events will be the ongoing run of the venerated jazz singer Annie Ross and the return of Marilyn Maye, an outstanding veteran vocalist whom more listeners ought to know about. For those whose preferences run toward the exotic, such as blond German songstresses in male drag, there’s the Weimar-centric cabaret of Karen Kohler and Micaela Leon, as represented by Fraulein Leon’s appearances at the Café Sabarasky at Neue Galerie (April 19 & 26).