“May you live to be 100, and may the last voice you hear be mine” was one of Frank Sinatra’s most legendary quotes — one that’s currently doing double duty as the theme of a yearlong career retrospective celebrating the 100-year anniversary of his birth (December 12, 1915). But consider this sentiment also something of a challenge to the dozen-plus stars who dared to tackle some of his most iconic songs at a tribute filmed December 2 in Las Vegas for Sinatra 100: An All-Star Grammy Concert, set to air Sunday, December 6 on CBS at 9 p.m. Could some of pop’s biggest names possibly leave a memorable stamp on songs already so imprinted onto one set of pipes?

The answer was yes, but only in certain instances. Sinatra embodied many personae in his nearly 75-year career — the crooner, the matinee idol, the well-connected Italian with rumored mob ties, the blue-eyed womanizer, the Jack Daniels–swilling rapscallion, the Vegas player — and often all at once. So the artists who were able to take on at least two or three of those attributes in their performances found the best results: Harry Connick Jr.’s almost-too-effortless “Luck Be a Lady” (upon flubbing the words in the third verse, Connick crowed, “And I don’t even drink!”), Seth MacFarlane’s booze-soaked “One for My Baby” (sung on an actual barstool), and Usher’s chewy “That’s Life” (complete with a flip of the bird and a hat-tossing key change). Most thrilling of all was Lady Gaga’s gender-bending “New York, New York,” for which the pop star donned her own take on Sinatra’s classic tux, hit on all the ginger-haired dancers (“Good to see ya, doll!”), and soft-shoed her way into the night.

Others played it safer, opting to honor the legacy of Sinatra’s inimitable Capitol era (1953–1961) rather than the full arc of his legacy. Celine Dion and Tony Bennett trotted out their well-known covers of “All the Way” and “I’ve Got the World on a String,” John Legend made “Young at Heart” newly wistful, and Alicia Keys proved the