PLAYBOY’S PENTHOUSE, PART 3 - "BEST EPISODE EVER" (and yet another TALE OF TONY)
February 13th, 1960: Count Basie, Joe Williams, Tony Bennett, Dave Lambert, Jon Hendricks, Annie Ross … and Phyllis Diller!
As previously mentioned, only four episodes of Playboy’s Penthouse have been made legally available, contained as part of two DVD packages, which are now even in themselves hard to find. Perhaps the single greatest episode, certainly musically speaking, is the 17th show, telecast on February 13th, 1960, roughly two weeks before the opening of the original Playboy Club in Chicago on February 29. Thankfully, at least one generous soul has posted this on YouTube, from the DVD. As Hugh Hefner describes it, this is “One of the all-time greatest parties we’ve ever had!”
Here’s the opening theme and the first segment: after the theme, we see Hugh Hefner in mid-conversation with Joe Williams. After Hef’s intro, Joe sings the jazz standard “Sometimes I’m Happy,” backed by no less than Count Basie himself and his current rhythm section, with the perennial Freddie Green on guitar, plus bassist Eddie Jones and superstar drummer Sonny Payne. It’s a fun, swinging opener. At about 4:30 in, they switch grooves and deliver a slow, mournful blues, “Five O’Clock in the Morning,” which we remember from the Roulette album, Breakfast Dance and Barbecue, recorded at the Americana Hotel in Miami in 1959. (There’s another episode where Big Joe is present, but Basie is not - and thus Joe is accompanied by Earl “Fatha” Hines.) At the end of the segment, Tony Bennett walks in and is warmly greeted by Hef.
“Sometimes I’m Happy” (Vincent Youmans & Clifford Grey, show: Hit the Deck)
“Five O’Clock in the Morning (blues)” (Joe Williams)


In the three years or so that Dave Lambert, Jon Hendricks, and Annie Ross toured as a working trio, they only made a handful of TV appearances, and their three different episodes of Playboy’s Penthouse are the central item in their video canon. They get no less than five full numbers here (the other two come later in the show), starting with two LHR classics based on tunes by Horace Silver. These weren’t included on any LHR albums but rather on a very rare 45 RPM single issued with a unique art cover by United Artists Records, which represents their last session before they signed with Columbia Records in 1959 and made their three classic albums for that label. “Every Day I Have the Blues” comes from their premiere album, Sing a Song of Basie, recorded for producer Creed Taylor at ABC Paramount Records in 1957, but this version of the classic Ernie Wilkins arrangement is even better than the one on the album in that it features both Count Basie and Joe Williams - in person. To see Annie Ross beeping right on the beat - like the trumpet section - throughout the second half of the number is worth the price of admission by itself.
“Spirit Feel” (Horace Silver)
“Doodlin’” (Horace Silver, lyrics by Jon Hendricks)
“Every Day I Have the Blues” (Peter Chatman, aka “Memphis Slim,” additional lyrics by Jon Hendricks)




I’m a big fan of the pioneering female stand-up comic Phyllis Diller (1917-2012) - not least for her role as the Bride of Frankenstein in the animated classic Mad Monster Party. Here she is at 43, and still near the start of a major career. She made herself the joke, constantly calling attention to how unattractive she was - especially in the context of a Playboy Penthouse party - but I always thought she was beautiful in her own way. She’s still somewhat stylishly-attired here; in later years her garb would grow ever more outrageous, with larger-than-life cigarette holders and enormously feathery headwear that amounted to a caricature of high fashion. This has to be an early example of what would become a standard trope for stand-ups: describing a flight on a commercial airline. One joke that wouldn’t fly today: at one point she gripes that the flight attendants were so old that she refers to them as “The Wright Sisters.” (Bonus Phyllis Diller during her amazing three-month run in Hello, Dolly 1969-1970.)
There’s no shortage of great Tony Bennett performances on TV from any era, and this is a particularly excellent document of Tony and the classic Ralph Sharon Trio with bassist Hal Gaylord and drummer Billy Exiner. (Tony refers to the group as a quartet - presumably referring to himself as the fourth member; at least, I don’t see or hear a guitarist or any other fourth musician.) Tony is much looser and more swinging here than in other more formal TV settings; alternating between swingers and ballads, he’s especially jazz on “You Can’t Love ‘Em All,” a lesser-known but worthy Cahn & Van Heusen opus in which Tony runs around the room and even gets surprisingly playful with the pitch near the end when he sings, “You can’t love ‘em all” and then repeats the phrase for good measure. I asked Daniel Weinstein what he thought Tony was doing here, and Daniel says: “In his last section, on the word ‘can't’ he purposefully sings, twice in a row, a bluesy high note drop. He knows what he's doing and he is not singing flat! There are plenty of other examples in his long career where he sings ‘on the low side’ of the pitch (though never completely off), but this isn't one of them.” Phyllis Diller is still there to kibitz, prompting Tony to sing the best version of “Climb Every Mountain” that I’ve ever heard. He concludes by paying homage to Hef’s hometown - and that of the Playboy Penthouse itself - with a brief chorus of the 1922 jazz standard “Chicago (That Toddlin' Town).”
“Just in Time” (Comden-Green/Styne, show: Bells Are Ringing)
“Love Walked In” (George & Ira Gershwin, film: The Goldwyn Follies)
“You Can’t Love ‘Em All” (Sammy Cahn & James Van Heusen, film: Say One For Me)
“Climb Every Mountain” (Rodgers & Hammerstein, show: The Sound of Music)
“Chicago (That Toddlin' Town)” (Fred Fisher)


And yet there’s more! The Lambert, Hendricks & Ross + Count Basie & Joe Williams super group gets two more numbers. We open with a shot that includes Annie, Tony, Hef, and an unnamed Playboy model in heated conversation. What’s special about this is that it’s highly likely that it was the first time Annie and Tony were in the same room at the same time; the two of them dated for a while and then they remained very close friends until Annie’s death at (almost) 90 in 2020. For the rest of his life, Tony always gave credit to Annie for conceiving the idea for the project that became his all-time favorite, The Tony Bennett - Bill Evans Album.
Annie Ross: “Twisted” (Wardell Gray & Annie Ross)
Lambert, Hendricks & Ross with Joe Williams: “The King” (Count Basie & Jon Hendricks)


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There's definitely a guitarist accompanying Tony on his last two numbers.