‘A Swinging Birdland Christmas’
With Klea Blackhurst, Billy Stritch, and Jim Caruso
Birdland, through December 25  

‘Christmas at Birdland (Deluxe Edition)’ (Club44 Records)

Early in the set, the three entertainers who star in “A Swinging Birdland Christmas” inform us that the show was inspired by the many television Christmas specials of the 1960s and ’70s — especially the annual holiday outings by the singer Andy Williams. To those who remember those shows (or, like myself, who watched them on DVDs and YouTube), this was already evident: The opening number included Williams’s signature seasonal song, “It’s The Holiday Season.”

What might not be apparent to everyone is that “A Swinging Birdland Christmas” is also, in the tradition of Williams, an inspired and highly stealthy mash-up of the most conservative pop music with the most radical.

The three stars here can all be seen regularly at Birdland: a singer, comic, and emcee who hosts the long-running Monday night open mic series “Cast Party,” Jim Caruso; an actress, singer, and endlessly entertaining musical comedy trouper, Klea Blackhurst; and a light-fingered jazz pianist who serves as musical director for many a marquee-name headliner and triples as an excellent singer himself, Billy Stritch.

Williams (1927-2012) in his time often seemed like the most plain vanilla of singing TV show hosts, a crooner with charm but none of Sinatra and Dean Martin’s sharp edge, or Bing Crosby’s antic wit and perfect timing. The most damning portrait of Williams is in the first memoir of Clive Davis, the accountant turned pop guru who, if he didn’t entirely invent the self-serving autobiography, certainly perfected it. 

In “Clive: Inside the Record Business” (1975), Mr. Davis explains how Williams dominated the “middle of the road” music market by relying on a very strict formula to create and market his albums. You can read it for yourself, but Mr. Davis convincingly portrays Williams as a soulless, hit-making automaton. 

The truth is somewhat deeper. On TV, Williams seemed like nothing more than an uber-nice guy with a beautiful voice but little personality, who was kind to everybody except a bear begging for cookies. (Yes, this was a running comedy bit on Williams’s show in 1969-’70). If you watch those shows and actually pay attention to the singing, though, a different impression emerges. In terms of his music, Williams was surprisingly hip; in the razor sharp arrangements by pianist Dave Grusin and others, Williams’s best performances encompass some amazingly progressive chord changes, modern harmonies, subtle modulations, and unexpected time signatures.  

Williams was especially enamored of a 1960s phenomenon, the jazz waltz; nearly every episode of “The Andy Williams Show” on NBC features a wildly swinging uptempo number in 3/4 time, a postmodern jazz innovation pioneered by Miles Davis and John Coltrane.

Williams was steered toward a more up-to-date model of traditional pop music through his long relationship — professional, personal, and even intimate — with Kay Thompson. Best known as the brilliant vocal arranger and singer who created the hip choral sounds of the 1940s MGM musicals, Thompson also literally invented the essential diva nightclub act, in which a larger-than-life leading lady is supported and surrounded by singing-and-dancing chorus boys — most famously the Williams Brothers, including the young Andy. Mitzi Gaynor, Janis Paige, and many others used this template, and especially Thompson’s best friend, Judy Garland, and, in tribute to the two of them, Liza Minnelli. 

Both Mr. Caruso and especially Mr. Stritch were close to Thompson through Ms. Minnelli, and “A Swinging Birdland Christmas” triumphs as a sparkling celebration not only of the holiday season but of the legacy of Kay Thompson and her greatest protegee, Andy Williams. The set is bookended by two Thompson-Williams classics, opening with “It’s the Holiday Season” and building to “Kay Thompson’s Jingle Bells,” and hitting “You Meet the Nicest People At Christmas” along the way.

The whole show — most of which is heard on the 2019 CD “Christmas at Birdland” (now reissued in a “deluxe edition”) — is full of worthy, mostly offbeat but upbeat holiday songs arrangement and delivered in this tradition of stealth hipness: advanced harmonies, surprisingly modish chords and key changes, not to mention nutso post-Dave Brubeck time signatures. There are also two songs from the late and legendary Freddy Cole, who for decades was the preeminent holiday star at Birdland, “Old Days, Old Times, Old Friends” and “Jingles the Christmas Cat,” a kitty considerably hipper than any reindeer, red-nosed or otherwise. 

There’s also a solo spot for bassist Steve Doyle, who sings and plucks on “A Holly Jolly Christmas,” on which the crowd sings along even before they’re invited to do so. Drummer Daniel Glass stands up and plays a solo with two sticks sans drums, then taps out the melody of “Little Drummer Boy” on the strings of Mr. Doyle’s bass a la “Big Noise from Winnetka.” 

“Jingle Bells,” which concludes the program, is presented as an abject lesson in how the seemingly simple can become deceptively profound.  Kay Thompson’s arrangement, duly noted on “The Andy Williams Christmas Album,” is full of unpredictable and abrupt shifts of key and time. Then, they encore with a mashup of more variations on the same theme, among them 1957 Gordon Jenkins/Sinatra treatment (the one in which the chorus chants “I love those J-i-n-g-l-e Bells”), the 1943 version by Bing Crosby with the Andrews Sisters, and Ella Fitzgerald’s fast-moving interpretation from “Ella Wishes You A Swinging Christmas” (1960).  Who knew a dumb little song like “Jingle Bells” — literally the symbol of musical simplicity — could be so rich and rewarding? Now, it’s got more twists and turns than Santa has reindeer.

Correction: 2012 was the year Andy Williams died. An incorrect year appeared in an earlier version.