On February 13 1960, Tony Bennett was a guest on the first season of Hugh Hefner’s TV show, Playboy’s Penthouse; this was almost exactly in between the inaugural of President Kennedy and the opening of the first Playboy Club, in Chicago (less than two weeks later). This particular show is a remarkable document of the singer at an early pinnacle. When Tony Bennett played the big concert houses, such as Carnegie Hall—where he debuted in 1962 (on the heels of “San Francisco”)—he had a full orchestra with strings behind him, and that was true of the major Vegas amphitheaters as well. But when he played at the Playboy, in the best tradition of the magazine, he cut everything down to the bare necessities. The 1960 show documents Tony working the way he would at the clubs just a short time later, with his most prolific accompanist, the brilliant Ralph Sharon, and a trio with bassist Hal Gaylor and Tony’s longtime drummer and sidekick Billy Exiner. It starts with Tony and Hef making small talk – joining them is Phyllis Diller, who has just done a comedy routine (and who’s in almost every shot of Tony’s segment and whose trademark cackle is heard throughout).
Looking immaculate in his tux, Tony and Ralph swing out with a bright, bouncy, opener “Just in Time,” a 1956 song from Bells are Ringing that Tony had already helped make into a standard with his highly-successful Columbia single. Seated next to Ralph on the piano bench, he takes out a pack of cigarettes and lights one. On a more serious note, he then sings what he announces as “an old Gershwin song,” namely “Love Walked In.” It’s serious, but never dire, Tony delivers it looking vaguely upwards, as if in prayer, with a joyful expression, even as Sharon supplies block chords reminiscent of George Shearing.
At this point, Tony briefly introduces the Ralph Sharon Trio, and lunges into “You Can’t Love ‘Em All” (a new Sammy Cahn – Jimmy Van Heusen song from the Marilyn Monroe movie Let’s Make Love). He’s especially playful here, toying with the melody and ad-libbing like crazy in a way that he wouldn’t have been able to in a more formal setting. He runs up a staircase on the line “there are mountains that you can move,” and dances his way down, exclaiming, “I feel like Fred Astaire.” In the second chorus, he does something that he may not have ever done elsewhere on film: just out of sheer capriciousness he hits some deliberate flat notes on the key word, “You can’t love ‘em all, no you can’t love ‘em all!”
Everyone’s spirits are unbelievably high, as the camera pans around and we see some of the other guests, among them Count Basie, Jon Hendricks, Dave Lambert, and Annie Ross. Still, somehow it’s Diller who requests the next song from Tony, asking for her favorite song from The Sound of Music, which had just opened on Broadway less than three months earlier. It’s a musical theater hymn that he sings without an overabundance of either piety or levity, a perfect balance of both; it’s reverent but not saccharine. I don’t think there’s ever been a more appealing version of this archetypical Rodgers and Hammerstein anthem.
Holding Diller’s hand – or at least her black opera glove – Tony then swings an exciting homage to what was already one of his favorite cities, the 1922 jazz classic “Chicago.” He’s even looser and more jubilant here, almost bouncing around the room, throwing in a reference to someone named “Eddie Hubbard” rather than “Billy Sunday” as the guy who was unable to shut down the windy city. As he heads towards a climax – literally surround with Diller to his right, Basie to his left, and Hefner in back of him – he does a few running-in-place style time steps, as if he’s got so much energy that singing isn’t enough, he’s got to be dancing at the same time.
It’s an amazing and unique moment. It’s almost as if Hugh Hefner and Tony Bennett are single-handedly christening the new decade, the new administration, and the new era of entertainment that was about to come, all in a single stroke.
We are extremely fortunate that this show exists, and that it has been issued on home video. Here is a link to Tony’s entire 10-minute segment, with all four songs: Tony Bennett complete segment Playboy’s Penthouse (February 13, 1960)
To be continued.
You can read more stories in my books Playboy Swings and The Persian Room Presents