Tony Bennett’s last Christmas with zany ‘Late Night’ host Conan O’Brien

Revered butterscotch baritone Tony Bennett confronted Alzheimer’s disease with dignity and maintained twice-weekly, informal rehearsals with pianist Lee Musiker inside his spacious New York City apartment until his July 21, 2023, passing at age 96. A perennial guest on the late night talk show circuit, particularly with Johnny Carson, Bennett befriended successor Conan O’Brien in 1993, debuting during the first season of Late Night with Conan O’Brien when the lanky, carrot-topped Irishman was struggling mightily to retain his late night perch amidst scathing reviews.

On Dec. 11, 2009, a mere six weeks before O’Brien controversially abdicated his seven and a half month reign as host of The Tonight Show, Bennett continued his annual holiday tradition of appearing on O’Brien’s late night show with an intimate reading of “Have Yourself a Merry Little Christmas,” first cut in the studio for 1968’s Snowfall: The Tony Bennett Christmas Album and overhauled by a Count Basie band arrangement exactly 40 years later on A Swingin’ Christmas, rounding out Bennett’s holiday LP triumvirate.

With a four-piece combo featuring band leader Lee Musiker on piano, former Count Basie sideman Harold Jones on drums, Gray Sargent on electric guitar, and Paul Langosch on stand-up bass, Bennett and his backing cats explored every nook and cranny of “Have Yourself a Merry Little Christmas.” Frank Sinatra referred to Bennett as his favorite singer, and listening to Bennett breathe life into each verse felt like a reunion with an old friend.

Scatting playfully, Bennett encouraged piano and guitar solos. Max Weinberg and the Tonight Show Band lent their considerable musical chops to the song’s dynamic finale. Though he wasn’t able to hit every high note compared to his heyday, Bennett proved why he was such an esteemed interpreter of America’s jazz tapestry. Music clips from O’Brien’s entire late night oeuvre involve costly rights clearance and are notoriously surrounded by red tape and not on YouTube. Luckily, the Japanese-based Nicotter does stream Bennett’s performance of “Have Yourself a Merry Little Christmas” minus the interview segment. Watch below.

Awash in thunderous applause, Bennett was then invited over to O’Brien’s desk for a fleeting conversation. Recalling his appearance on the inaugural Tonight Show Starring Johnny Carson in 1962, Bennett listed Mildred Pierce Oscar winner Joan Crawford and ad-lib pros Groucho Marx and Mel Brooks as also among the guest roster on that historic slice of television. The “Cold, Cold Heart” song stylist remembered, “At the end of the show we all got up and Johnny said, “That’s the first show. Let’s see how it goes.” O’Brien chimed in, “It worked out pretty well.” He wasn’t kidding. Carson went on to helm 30 seasons of The Tonight Show that have never since become so engrained in the collective conscious.

Bennett divulged that he had signed an extension to his contract with Columbia, originally drawn up in 1951. Barring a wilderness period between 1972 and 1986 when substance addiction, the Internal Revenue Service, choosing ill-suited songs for the studio, and plummeting record sales made him passé, Bennett’s home remained the label that also counted Bob Dylan and Bruce Springsteen among its legendary client roster.

A jazz album with none other than Stevie Wonder and Grammy-nabbing producer Quincy Jones was Bennett’s next tantalizing admission, but no such collaboration ever materialized, although two earlier Bennett-Wonder duets are available — “Everyday (I Have the Blues),” from 2001’s Playin’ with My Friends: Bennett Sings the Blues, and “For Once in My Life,” track 11 on the 2006 platinum-selling Duets: An American Classic.

Bennett’s summit with O’Brien was a classy farewell, marking his 16th and final appearance for reasons that are unclear. Within a year O’Brien leaped over to basic cable channel TBS for a decade of Conan, the continuation of his late night kingdom shot on Stage 15 of the Warner Bros. lot in Burbank. Bennett subsequently paid four visits to The Tonight Show Starring Jimmy Fallon. Hours after Bennett’s death was announced, the Harvard-educated O’Brien eloquently shared on Twitter, “Tony Bennett was a rare combination of extraordinarily talented, engagingly funny, and genuinely kind. Thank you, Tony, for giving us so many special moments.”

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