Tony Bennett’s final Christmas performance with Conan O’Brien

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Tony Bennett guested a record 16 times on Conan O’Brien’s absurd NBC late night shows, always during Christmas. The Italian crooner’s final 2009 visit is reviewed in-depth here. Seen above, Bennett basks in the audience’s rapt adulation after delivering a spot-on rendition of “Have Yourself a Merry Little Christmas” on “The Tonight Show with Conan O’Brien,” December 11, 2009. Photography by Paul Drinkwater / NBCU Photo Bank / Getty Images

Revered Italian crooner Tony Bennett shows no signs of retiring just yet. Always a perennial guest on the late night talk show circuit, particularly Johnny Carson, the nonagenarian 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 in the midst of scathing reviews.

On December 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 a laid-back performance of “Have Yourself a Merry Little Christmas,” first recorded in the studio for 1968’s Snowfall: The Tony Bennett Christmas Album and subsequently given a Count Basie band arrangement exactly 40 years later on A Swingin’ Christmas, to thunderous applause. The occasion marked his 16th and apparently final appearance with O’Brien for reasons that are unclear as of this writing [Bennett subsequently paid two Christmas visits to The Tonight Show Starring Jimmy Fallon in 2014 and 2016].

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 band were in fine form.

Frank Sinatra referred to Bennett as his favorite singer on numerous occasions, and listening to Bennett breathe life into “Have Yourself a Merry Little Christmas” felt like a fine wine. Scatting playfully during the song’s verses, Bennett encouraged both piano and guitar solos as the audience signaled their approval.

Max Weinberg and the Tonight Show Band lent their considerable musical chops to the song’s exciting finish. Though he may not be able to hit every high note as in years past, Bennett truly proved why he is such an esteemed interpreter of America’s jazz tapestry.

After the rousing performance, O’Brien invited his very special guest to sit down for a mini interview. Recalling his appearance on the very first episode of The Tonight Show Starring Johnny Carson 47 years earlier, Bennett listed actress Joan Crawford and comedians Groucho Marx and Mel Brooks as also appearing on that historic television moment.

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, as Carson went on to helm 30 hugely successful seasons of The Tonight Show that have never been duplicated.

Bennett revealed that he had signed a new contract with Columbia Sony Records and must hold a world record for remaining with a label for such an extended period — since 1951 in fact — barring a wilderness period between 1972 and 1986 when substance addiction, an indifferent attitude to recording, and plummeting record sales because of changing listening trends made him seem passé.

Before signing off, Bennett revealed his next album would be a jazz project with Stevie Wonder, and Quincy Jones would serve as producer. Such an extended collaboration has inexplicably not materialized, although two duets are available — “Everyday (I Have the Blues)” [2001’s Playin’ with My Friends: Bennett Sings the Blues] — and “For Once in My Life” [the 2006 platinum-selling project Duets: An American Classic].

If it was indeed Bennett’s last summit with O’Brien, he went out in fabulous style. Check out the video below as well as an earlier 1999 visit to Late Night when the elegant balladeer raised the roof delivering Duke Ellington’s “I’m Just a Lucky So and So.”

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Tony Bennett shoots the breeze with brief “Tonight Show” host Conan O’Brien on December 11, 2009. Photography by Paul Drinkwater / NBCU Photo Bank / Getty Images
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On December 11, 2009, innovative jazz stylist Tony Bennett effectively tackles “Have Yourself a Merry Little Christmas” on “The Tonight Show with Conan O’Brien.” Pianist Lee Musiker is on piano while Gray Sargent provides some tasty electric guitar licks. Photography by Paul Drinkwater / NBCU Photo Bank / Getty Images
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Ninety-year-old artistically vital American songbook master Tony Bennett packs a sold-out house at the Times Union Center for the Performing Arts — Moran Theater in Jacksonville, Florida, on February 22, 2017. Photography by Jeremy Roberts
Click to watch Tony Bennett visit the classic “Late Night with Conan O’Brien” NBC comedy-talk show series to croon a remarkable rendition of Duke Ellington’s “I’m Just a Lucky So and So” on December 17, 1999. Video Credit: Broadway Video / Conaco / Universal Media Studios

© Jeremy Roberts, 2009, 2017. All rights reserved. To touch base, email and mention which story led you my way. I appreciate it sincerely.

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Retro pop culture interviews & lovin’ someone fierce sustain this University of Georgia Master of Agricultural Leadership alum. Email:

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