A 30-minute phone conversation with Nellie McKay can cover a lot of ground: literary-political figures like James Baldwin, Howard Zinn, Dalton Trumbo, and Zora Neale Hurston; executed convicted murderer Barbara Graham; and, of course, lots of musicians, including John Lennon, Dinah Washington, Dave Frishberg, Bob Dorough, Billy Tipton, Richard and Mimi Farina, and Frank Zappa.
The 36-year-old singer, songwriter, actor, and activist — who comes to City Winery on Nov. 1 — has rarely been contained by easy categories. That’s been true since her audacious 2004 debut, on Columbia, “Get Away From Me.” That double-disc release (it’s title widely seen as a response to Norah Jones’s breakout hit of a few years before, “Come Away With Me”) sported 18 originals — pop-rock, rap, and songs whose forms and lyrics owed a lot to the flowering of the mid-20th-century Great American Songbook.
Since then, there have been six more albums alternating originals and covers (including “Normal as Blueberry Pie: A Tribute to Doris Day”), three self-penned solo-performance musical-theater portraits (of Graham, transgender musician Tipton, and comedian Joan Rivers), an award-winning turn as Polly Peachum in the Roundabout Theatre production of “The Threepenny Opera,” with Alan Cumming, and a through-theme as activist and animal rights spokeswoman..
Her latest CD, “Sister Orchid,” is a selection of mostly American Songbook standards that includes Rodgers and Hart’s “My Romance” (set to a circus calliope oom-pah-pah beat); Ann Ronell’s “Willow Weep for Me” (a contrasting triptych of the ballad, with the middle chorus set to boogie-woogie piano); Tom Adair and Matt Dennis’s Sinatra pity party “Everything Happens to Me”; and rarities like Johnny Mercer and Hoagy Carmichael’s “Lazybones” and Fran Landesman and Dorough’s “Small Day Tomorrow.”
But McKay says the City Winery show will be “a potpourri,” with requests invited — “especially for people who’ve come a long way, and they’ve hired a sitter, to hear that one song.” She said she’ll probably be paying special tribute to legendary engineer/producer Geoff Emerick, a longtime friend, who produced both “Get Away From Me” and 2015’s ’60s cover collection, “My Weekly Reader.” Emerick, who had worked with everyone from the Beatles (as George Martin’s right-hand man) to Cheap Trick and Elvis Costello, died of a heart attack on Oct. 2.
Thinking about her relationship with Emerick, McKay says, “The first album was a lot of pressure and a lot of money. Even so, we had a lot of fun. The second album was just magic. I really loved him.”
Mitchell Cohen, the A&R executive who put Emerick and McKay together on “Get Away From Me,” recalls, through e-mails and a phone call, “What was so magical about Nellie was all this contradiction in her. She sounded so sweet and warm, and then witty, biting, and subversive, and you wanted to get everything on the plate to see all the sides of her.”
In approaching Emerick, he says, “Obviously, the association with the Beatles was a selling point.” But the clincher was Emerick’s production of Costello’s “Imperial Bedroom” — “in terms of musical sophistication, attention to detail, respect for the songs.”
In reaching out to Emerick, Cohen remembers balancing the desire of a brilliant young performer “who clearly wanted to be in creative control” — McKay was 21 at the time — and Columbia’s demand “to have someone in the room who knew the ropes.”
It makes sense that Cohen (who later brought McKay to Verve for the Doris Day album) would want a steady hand at the tiller for the peripatetic McKay. In a show at the Regattabar last June, McKay accompanied herself at the piano and on ukulele and harmonica, from standards and her own “Wizard of Oz” paranoid fantasy, “Toto Dies,” to Gerry and the Pacemakers’ 1964 hit “Don’t Let the Sun Catch You Crying,” the Farinas’ anti-imperialist murder ballad “Bold Marauder,” Zappa’s scabrous LBJ-era “Great Society” satire “Hungry Freaks, Daddy,” and the Cyrkle’s 1966 hit “Red Rubber Ball” (written by Paul Simon and the Seekers’ Bruce Woodley). That last is one of the finer romantic pop chestnuts from “My Weekly Reader.”
“I always did that song when I was playing piano bars,” McKay says. “Then we did it for the ’60s album. Geoff, of course, recorded the original. You have to pinch yourself now and then.”
Even when she’s digging deep into 1960s folk-rock, McKay’s arrangements (mostly voice and piano), bell-clear vocal chops, and savvy phrasing put her in the camp of cabaret singing — a style halfway between jazz and musical theater that emphasizes textural clarity and fully drawn characterizations. Her love of old movies, Day, and the ’60s material, she says, comes from her mother, Robin Pappas (who separated from McKay’s father, English writer-director Malcolm McKay, early on).
There are all manner of odd bits and idiosyncrasies in McKay’s readings, like the accent that shows up now and then, underlining the English music hall strain in British invasion hits like Herman’s Hermits’ “Mrs. Brown, You’ve Got a Lovely Daughter,” but also her own manic-phase chronicle “Ding Dong.”
“I say it’s lovely if you can channel someone else,” McKay says. The accent, she allows, could come from her early childhood in England but might also be influenced by the “dipsomaniac” role played by Ronald Colman in “A Tale of Two Cities” (1935), a movie she was introduced to in a film series based on Baldwin’s book-length essay on the movies, “The Devil Finds Work.”
‘[It will be] a potpourri [with requests invited], especially for people who’ve come a long way, and they’ve hired a sitter, to hear that one song.’
That reference leads to a ping-ponging discussion of England during the Blitz, Zinn’s essay “Just and Unjust War,” Trumbo’s “Johnny Got His Gun,” and Hurston’s characterization of Harry Truman as “the butcher of Asia.”
These scattershot references are somehow all of a piece with McKay’s unwavering commitment to her material. That’s why a one-woman show like “A Girl Named Bill: The Life and Times of Billy Tipton,” which McKay also performed at the Regattabar a couple of years back, holds together (including Jimmy Durante’s “Inka Dinka Doo,” replete with a vocal impersonation of the Schnoz). One can imagine that single-mindedness also carries McKay through the anti-death-penalty sentiment of “I Want to Live!,” the Graham piece that’s drawn equally from the Susan Hayward movie of that title and McKay’s own research (as McKay describes it, “a death-row musical revue”).
You get the feeling that even as McKay is playing scores of different characters, she’s all of them.
So, if McKay loves a song, is there anything that prevents her from singing it? “Yeah, for sure, there are things that you can’t do, such as ‘This Bitter Earth.’ It was recorded by Dinah Washington. I would have loved to have put that on the album. But there’s no touching it. At least by me.”
At City Winery, Boston, Nov. 1 at 8 p.m. Tickets $20-$30, 617-933-8047, citywinery.com/boston/Jon Garelick can be reached at firstname.lastname@example.org. Follow him on Twitter @jgarelick.