“How does it feel?” The tone in which those four words are delivered is a critical factor in determining the psychic damage wrought by Bob Dylan’s musical missile, “Like a Rolling Stone.” When the jazz singer Paula West sang them at the Oak Room of the Algonquin Hotel on Tuesday evening, she underplayed the composer’s crowing sarcasm and the song emerged in a softer light.

Yes, “Like a Rolling Stone” will always be a hipster’s savagely gleeful portrait of a privileged princess’s downfall. But as Ms. West asked how it felt in a quiet, urgent voice, empathy overcame contempt; there but for the grace of God.

Ms. West’s affinity for Bob Dylan, whose songs she regularly puts into her shows, recalls the passion for his music expressed by Nina Simone, another black female singer who went even farther in personalizing his lyrics. Like Ms. Simone and like Cassandra Wilson, who also goes any musical place that suits her, Ms. West refuses to be bound by categories.

Her new show, which plays through Nov. 11, casts the widest net, so far. “Like a Rolling Stone” is sandwiched between “Bewitched, Bothered and Bewildered” and “It Ain’t Necessarily So” in a set that includes “Softly, as in a Morning Sunrise,” from “The New Moon,” arranged as a sultry bolero, and a pop-jazz “Loch Lomond” sung back to back with “Danny Boy.” Behind her, the George Mesterhazy quartet stretches with her from Scotland to Nashville.

To everything she sings, Ms. West brings an ever-deepening feel for the blues. Her voice, though reminiscent of both Ms. Simone’s and Ms. Wilson’s, has a thicker caramel coating. This sound was the focus of an attenuated version of that archetypal torch song, “Why Was I Born?,” in which she lingered over the words at the ends of phrases as though the answers to the song’s metaphysical questions lay buried in the texture of her own voice.

For all her stylistic wanderings, Ms. West always returns to home base, a place where blues and jazz songs are inflected with a sly, humorous appreciation of the absurd and the naughty. She turned Leonard Feather’s breezy “Man Wanted,” a desperate woman’s humorous personal ad for a man “young or old, fat or lean, hot or cold, kind or mean” into a tongue-in-cheek frolic.

Finally came her signature song, “The Snake,” Oscar Brown Jr.’s urban folk tale about a woman’s fatal attraction to a poisonous reptile who hustles her; this bit of caramel dosed with arsenic made a tasty encore.