Most Overrated Singer:

Barbra Streisand. Many singers make my teeth ache, from Rudy Vallee to Britney Spears, but none is taken so seriously as the incomparably ersatz Barbra Streisand. She is an icon of America’s love of display and personality at the expense of sincerity and taste. Everything she sings is charged with self-loving vulgarity; worship me, she bellows, and forget the song. Streisand has a huge instrument and not an inkling of what to do with it. Her primary technique consists of heavy breathing, which turns tenaciously aspirate on vowels or h words. As a small boy, watching her in Funny Girl on Broadway, I recoiled at her shallowness. She never deigned to play the role; she was too intent on stopping the show. Alice Paye, who played a similar part in Rose of Washington Square , displayed more soul on her worst day. Classical Barbra exposed her hubris, yet her pop singing is every bit as garish. Vulgarity has its place, but only when animated by emotional generosity, which is why, despite her immense popularity, Streisand has never joined the ranks of the great hearts-on-their-sleeves emoters, from Jolson to Garland. They meant it. She doesn’t.

Most Underrated Singer:

Bing Crosby. It would have been inconceivable to call Bing Crosby underrated at any time between 1931 and 1965. He was the most popular, admired, and beloved singer the world had ever known. In those years my answer would have been Louis Armstrong or Ethel Waters, who with Crosby invented America’s modern vernacular style. But Armstrong at long last routinely receives his due, and much of Waters’s work is sadly dated, while the ocean has rolled over Der Bingle. The tide will change. He is still admired for his jazz records (one bandleader called him “the first hip white person born in the United States”), but no less gratifying is his unparalleled versatility. With his perfect time and articulation, Bing could be equally affecting on country, cowboy, Hawaiian, and standard songs. We tend to think of the swing era as pounding feet and flying skirts, but listen to Crosby’s great Depression waltzes—“Mexicali Rose,” “The One Rose”—and you hear the sober, tremulous flip side of those years. I once saw a skeptical opera expert reduced to tears by Bing’s “Sweetheart of Sigma Chi,” of all things. No one captured the heartbeat of this nation during the 1930s and 1940s as well as he did, and his best work continues to speak volumes.