Fred Astaire was known to many in the 1930s as a Broadway stage and Hollywood screen dancer. But Bennett loves Astaire for introducing a Cole Porter song to the public when he sang it in the 1932 film, "The Gay Divorcee."
Bennett explains that Astaire's version of "Night and Day" makes his playlist because "it's a song that everybody adores when they hear it. It's a great, great song. … All the great composers, Ervin Berlin, George Gershwin and Ira Gershwin, Johnny Mercer, you know — when they wrote a song, and this was in the '20s and '30s they said the only one that introduce it is Fred Astaire."
"[Astaire's] an amazing performer and songs like 'They Can't Take That Away From Me' and 'Isn't It a Lovely Day to Get Caught in the Rain,' 'Foggy Day in Londontown' — all these great, great songs were introduced by Fred Astaire," said Bennett. "Everybody thinks of him as a dancer, but he actually created the great American songbook."
Frank Sinatra's 1955 album, "In the Wee Small Hours of the Morning," had a thematic mood of isolation and love lost. In 2003, Rolling Stone magazine ranked it No. 100 in its list of the 500 greatest albums of all time. The title track from the album is also much adored by Bennett.
"My master is Frank Sinatra," Bennett said. "'In the Wee Small Hours of the Morning' … Sinatra would have called it a saloon song, which is really fantastic. It's the opposite of working in a huge stadium like they do today. Millions and millions of people so up like a football game. It's very intimate so that the artist sings just to you, not to 10,000 people and uh, that's how everybody started in show business."
Johnny Mercer, hailing from Savannah, Ga., was known in the 1930s-'60s as a popular songwriter and singer. He wrote lyrics to more than 1,000 songs in his lifetime including "Emily." Bennett said, "No one wrote American lyrics than Johnny Mercer."
The reason Bennett likes Mercer's song "Emily" is because "[Mercer] invented a word, and that's what Shakespeare was famous for, and in the song he said when my eyes visualize a family, I see dreamily, Emily too. So the word dreamily was never written before. He was so creative, he invented words that were never said before. He had the God-given gift of knowing how to write with American lyrics, not British lyrics, but American lyrics."
In the late 1980s, a female vocalist hit the American pop-music scene. One of her biggest fans is Bennett.
"I love k.d. lang. I just love the way she sings. Anything she sings. She's that way. Very genuine," said Bennett.
One of his favorite songs she performs is "If We Never Meet Again," calling it "a great little song."
"She's so honest and sincere and wholesome," said Bennett. "She's very, very clear about herself. I mean outside of Judy Garland, I think she's the best singer I've ever heard for popular singing."
In 2002, Bennett and lang released an album together entitled "A Wonderful World."