Max Raabe, the wry, unsmiling and nonchalantly charismatic vocalist who headlines the Palast Orchester of Berlin, opened the ambitious 17-day festival Berlin in Lights on Friday night at Carnegie Hall. As is his wont, Mr. Raabe gave running commentary on the songs he and the ensemble were performing.

Introducing one number in his world-weary way, he said that music “has always been closely linked to destiny and personal tragedy.” Staring at the audience and hesitating for a beat (his comic timing is flawless), he added, “Who cares?”

Then he segued into “Who’s Afraid of the Big, Bad Wolf?” the Frank Churchill song written for the 1933 animated Disney short “The Three Little Pigs.” Mr. Raabe was joined by three good sports from the orchestra, who sang the roles of the pigs.

Mr. Raabe’s quip about the deeper meaning of music said much about the aesthetic of the 12-piece Palast Orchester, which is celebrating 20 years of performing German popular and cabaret songs from the Weimar era and American songs of the time that gained popularity in Europe.

Mr. Raabe maintains a detached attitude about the matter. In his own way he is a tenderly expressive singer with a light baritone voice, though, like Fred Astaire, he can croon his way to tenorial highs or dip to playfully earthy basso lows. But there is not a trace of sentimentality in his singing, not a slice of ham, even when he is having fun. When Mr. Raabe, backed by the musicians playing the band’s harmonically rich, casually jazzy and inventive arrangements, performs a breezy romantic song like the 1929 “Wenn du von mir fortgehst” by Hans May and Kurt Schwabach, it comes across as affecting and piercingly true.

The program provided neither a list of songs nor English translations for the German ones. But after hearing Mr. Raabe’s sardonic spoken summaries of the lyrics, even those with scant knowledge of German must have picked up the textual nuances from his sly performances. Take “Du bist meine Greta Garbo,” by Robert Stolz, with lyrics by Walter Reisch. What is it about? The danger of a man comparing his lady to another lady, Mr. Raabe said. “You are my Greta Garbo,” he explained “You are as blond and as beautiful.” Then he added, after another pregnant pause, “but not as rich.” This was all you needed to know.

Mr. Raabe, 44, began his musical life singing in a boys’ choir in the Westphalia region of Germany, and that background affects his artistry today. Rail thin, impeccably tuxedoed, his fair haired slicked back, Mr. Raabe comes across as a wised-up adult choirboy with a slightly seductive glint in his eye.

It was fascinating to hear him in “Cheek to Cheek,” the Irving Berlin standard that will forever be associated with Astaire. If Mr. Raabe lacked the dancer’s swing of Astaire’s singing, he brought a slippery legato wistfulness to the song that made you hear it freshly.

The Palast musicians, all male except for the solo violinist Cecilia Crisafulli, play with a stylishness, grace and vitality that do not call attention to their impressive virtuosity. Versatile as well, they double up and even triple up on instruments. Rainer Fox, for example, played baritone saxophone, the rarely heard bass saxophone and clarinet, and was a supporting vocalist.

Though there were three encores, the final piece on the formal program, “Cosi Cosa,” from the 1935 Marx Brothers film, “A Night at the Opera,” again captured the art of ambiguity that characterizes Mr. Raabe and the Palast Orchester. The lyrics try to explain what the phrase “Cosi Cosa” means. Does it mean yes? Or no? Well, yes and no.

-Anthony Tommasini