The Bootleg Files: Frank Sinatra Hosts ‘The Tonight Show’

BOOTLEG FILES 774: “Frank Sinatra Hosts ‘The Tonight Show’” (1977 episode with Sinatra filling in for Johnny Carson).

LAST SEEN: On YouTube.


REASON FOR BOOTLEG STATUS: There might be a problem with music clearance rights.


Frank Sinatra did not give many interviews – he certainly didn’t need the publicity, nor did he welcome questions about his personal life that he considered to be intrusive. But there was one time in Sinatra’s life when he had the opportunity to be the one asking the questions – and, believe it or not, he was very good at it.

On November 14, 1977, Sinatra agreed to fill in for a vacationing Johnny Carson as a guest host on “The Tonight Show.” During the Carson years, a remarkable constellation of stars temporarily inhabited the hosting duties including Jerry Lewis, Orson Welles, Burt Reynolds and Woody Allen; Carson broke the color barrier when Sammy Davis Jr. guest-hosted in 1965 and the gender barrier the same year when Broadway star Phyllis Newman occupied his chair.

Sinatra was brought in because he had a pair of NBC productions coming up that would benefit from his presence on this popular late-night show: the made-for-television movie “Contract on Cherry Street” – FWIW, some scenes from that film were shot around the corner from my childhood home in the Bronx – and the Dean Martin roast that had Sinatra in the spotlight. Three of the celebrities booked as guests for this episode also had NBC connections – George Burns had an upcoming variety special on the network, Angie Dickinson was the star of the top-rated “Police Woman” and Carroll O’Connor was starring in an NBC-produced remake of “The Last Hurrah.”

The episode opens with a tuxedo-clad Ed McMahon announcing, “And now, here’s Ol’ Blue Eyes!” – and a tuxedo-clad Sinatra emerges to thunderous applause. (The NBC Orchestra under Doc Severinsen were also all in tuxedoes for this show.) Sinatra offers the audience a jaunty “Hiya, gang!” and begins to launch into the song “Maybe This Time,” but the applause only grows louder – the camera switches to the audience, who have elevated from their seats for a standing ovation.

Sinatra’s take on “Maybe This Time” is radically different from Liza Minnelli’s version from the film “Cabaret,” where she offered a pessimistic consideration of finding elusive love. Sinatra, however, presented it with self-confident pugnacity, like a gambler who knows his next roll of the dice will produce a seven. His follow up tune, “See the Show Again” – which he credits to “young Barry Manilow” – is served with a gentle sincerity of someone who is uncertain if he wore out his welcome. (Sinatra also credited John Kander and Fred Ebb for penning “Maybe This Time” and the arrangers for both of the numbers.)

While Sinatra didn’t have any additional songs, he graciously played the butt of jokes in much of the episode’s comedy segments. McMahon worked with him on an alleged series of letters that Sinatra wrote to prominent figures that comically riffed on his supposedly rough and gruff demeanor – in a letter to the outspoken then-U.N. Ambassador Andrew Young, Sinatra’s letter recommended that he brush his teeth with Elmer’s Glue.

Later, George Burns recruits Sinatra for a duet on “By the Light of Silvery Moon,” leaving an increasingly baffled Sinatra waiting until for cue that doesn’t pop up until the final few bars. And the night’s last guest, Don Rickles, runs amok with Sinatra with Mafia-themed jokes and a hilarious sight gag that imagines Sinatra’s wife Barbara toppling over due to excessive jewelry she is wearing.

But when the time comes for conversations with his guests, Sinatra displays a knack for asking off-beat questions – he quizzes Burns about Al Jolson and gets into a lengthy talk with Dickinson about speeding and traffic safety, of all things. But unlike the emetically smug Kimmel-Colbert-Fallon-Corden-Meyers bunch that spoil today’s late night, Sinatra is clearly listening to what his guests are saying and is asks intelligent follow-up questions. Even better, Sinatra is clearly enjoying himself in this unlikely role of inquisitor – and his talk with Dickinson their collaboration in the film “Ocean’s 11” is warm and charming.

The episode has one misfit: comic John Barbour doing a labored and tiresome stand-up routine. He is not invited to join the other stars on the couch, and his exile is deserved. And some woke viewers might considered a few of the 1977-era jokes to be politically incorrect, but they clearly were not done in malice and can still generate laughs from those who aren’t touchy about everything.

The Carson estate has yet to offer a home entertainment re-release any of “The Tonight Show” episodes with the guest hosts that filled in for Carson. Bits and pieces of this episode floated around YouTube for years, but last month the almost-complete version was uploaded in a not-quite-pristine unauthorized posting – the Barbour segment was scissored out, which is fine because Barbour presented it on his YouTube channel.

Anyone who is a Sinatra fan must set time aside to enjoy Sinatra’s spin as a talk show host. In many ways, this was one of the very best episodes in the history of “The Tonight Show.”

IMPORTANT NOTICE: While this weekly column acknowledges the presence of rare film and television productions through the so-called collector-to-collector market, this should not be seen as encouraging or condoning the unauthorized duplication and distribution of copyright-protected material, either through DVDs or Blu-ray discs or through postings on Internet video sites.

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