GoldfingerDuring today’s walk the iPod segued from Shirley Bassey doing the theme from Goldfinger to Frank Sinatra singing “Day in, Day out.” It made me think, as I often do, of a lost opportunity. I wish Sinatra had played Felix Leiter in the James Bond films.

Leiter, for all who don’t know this important fact, was 007’s CIA connection. The character appeared in several of Ian Fleming’s Bond novels, and also showed up in the movies—usually played by a different actor each time. Jack Lord was perfectly adequate in the role opposite Sean Connery’s Bond for the first film, Dr. No, but things went downhill from there. In Goldfinger, Leiter was played by charisma-challenged Canadian actor Cec Linder. Cec Linder! Suffice it to say, you can easily imagine Linder’s Leiter taking a break from his agency duties to peddle Fuller brushes door to door. In Thunderball, Leiter shows up in the guise of an actor named Rik Van Nutter. I’ve seen the movie several times and I can barely remember him.

But there is a parallel universe, one that’s just a little better than ours, where Sinatra did play Leiter. Here’s an excerpt from a film history published in that alternate universe:

“Sinatra had already provided the vocals for the title song for From Russia with Love, so an on-screen teaming with Connery for Goldfinger seemed like a natural fit. ‘Sinatra brings a tough, wolfish American quality to the character of CIA agent Felix Leiter, and he meshes perfectly with Connery’s suave British spy,’ wrote Arthur Knight in his review of Goldfinger for Saturday Review. Producers Cubby Broccoli and Harry Saltzman immediately signed Sinatra to reprise his role in Thunderball. Before shooting, the actors demanded script rewrites. “Haggis [Connery] and I both thought the gadgets had run their course,” Sinatra told an interviewer. “We wanted to get back to pure spy stuff, like the books.” The result was the leanest, tautest Bond yet. Connery was so pleased with the result, he insisted Sinatra receive a cameo in the next film, On Her Majesty’s Secret Service (considered by most Bond fans to be the best of the series), and then agreed to give Sinatra co-billing on Diamonds Are Forever, a gritty revenge thriller that unfolds in the shadows behind the bright lights of Las Vegas. Sinatra went on to play Leiter in three “Agency” films, with diminishing results. The first film, The Agency (with Connery taking a cameo as Bond) was generally well received, but the last in the series, Leiter’s Out! degenerated into a grab bag of Rat Pack shenanigans with everyone from Joey Bishop to Sammy Davis, Jr., showing up to join in the alleged fun.”

In this different and better parallel universe, Richard Castellano reprises his role as Clemenza for Godfather II and George Lucas decides that three Star Wars films are enough.

(For those wanting a complete Leiter list, here’s one from the Internet Movie Database.