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

The “extraordinarily talented, engagingly funny, and genuinely kind” Tony Bennett guested a record 16 times on Conan O’Brien’s absurd NBC late night shows, always during Christmas. Don’t go anywhere if you wanna discover the Italian crooner’s final 2009 visit, packed with photos and videos. Seen above, the 90-year-old American songbook master keeps a rapt audience in the palm of his hand at the Times Union Center for the Performing Arts — Moran Theater in Jacksonville, Florida, on Feb. 22, 2017. Photography by Jeremy Roberts

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…