Sean Connery and Shirley Eaton in ‘Goldfinger’ (Photo: United Artists/Everett Collection)
Movie: Goldfinger (1964)
Sean Connery in ‘You Only Live Twice’ (Photo: United Artists/Everett Collection)
Movie: You Only Live Twice (1967)
Any time you look at films from a different era, you know that prevailing attitudes of the times don’t often match with modern ones. But the problem with Bond disguising himself as a Japanese fisherman to go undercover is not just how racially insensitive it is, but how unbelievable he looks. With his eye makeup and terrible toupee (even worse than the one Connery usually wore), you buy that Bond could have a helicopter in a suitcase more than the idea that anyone would ever mistake him for being Asian.
Putter Smith and Bruce Glover in ‘Diamonds Are Forever’ (Photo: United Artists/Everett Collection)
Mr. Wint and Mr. Kidd
Movie: Diamonds Are Forever (1971)
Connery left the series after “You Only Live Twice,” unhappy with how he had been treated by the producers. He was convinced to return for one more go-around in 1971 (to the tune of $1.25 million), but the result didn’t hold up to the standards of his earlier films. It’s got over-the-top performances from the supporting cast, including Jill St. John, Charles Gray as Blofeld, and future sausage magnate Jimmy Dean. Most egregious, though, are the characters of Mr. Wint (played by jazz musician Putter Smith) and Mr. Kidd (Bruce Glover, father of “Back to the Future” star Crispin). The pair of murderous henchman are presented as being a gay couple, and their whole subplot has a distinct tenor of homophobia.
Roger Moore and Yaphet Kotto in ‘Live and Let Die’ (Photo: United Artists/Everett Collection)
The Inflatable Bad Guy
Movie: Live and Let Die (1973)
There’s plenty of weirdness in Roger Moore’s first outing as 007. After “Shaft” was a surprise hit in 1971, the producers tried injecting blaxploitation elements into the Bond template, to sometimes cringe-worthy results. But after the cartoonish stereotypes, including 7-Up pitchman Geoffrey Holder as a face-painted voodoo practitioner, the suspension of disbelief literally pops at the end of the movie. Bond is fighting Kananga (Yaphet Kotto), and he forces a compressed air pellet into the villain’s mouth. Kananga blows up like a balloon, shoots up into the air and explodes. Bond then shamelessly comments, “He always did have an inflated opinion of himself.”
Christopher Lee and Maud Adams in ‘The Man With the Golden Gun’ (Photo: United Artists/Everett Collection)
Scaramanga’s Extra Nipple
Movie: The Man With the Golden Gun (1974)
So what was “Skyfall” director Sam Mendes’ choice for most embarrassing Bond moment? In a recent interview with Yahoo! Movies, he pointed to the scene in “The Man With the Golden Gun” where Christopher Lee, as the titular character Scaramanga, takes off his shirt to reveal his distinguishing feature: three nipples. Mendes said the dramatic music and camera work made what’s meant to be a big moment simply laughable. Just as bad: to impersonate Scaramanga, Q gives Bond a fake nipple to wear.
Richard Kiel and Blanche Ravalec in ‘Moonraker’ (Photo: United Artists/Everett Collection)
Jaws Gets a Girlfriend
Movie: Moonraker (1979)
“Moonraker” could probably get a top ten list all to itself. Intended to draft on the sci-fi wave from “Star Wars,” this one has plenty in it to be embarrassed about. From the Venetian gondola that turns into a hovercraft, to the Bond girl’s name (“Holly Goodhead”), to the indignity of 007 having to wear a shiny spacesuit. But the weirdest element has to be Jaws, the metal-mouth villain played by Richard Kiel first established in “The Spy Who Loved Me,” getting a love interest. The giant falls for a tiny blonde named Dolly with pigtails and braces (naturally).
Roger Moore and Grace Jones in ‘A View to a Kill’ (Photo: United Artists/Everett Collection)
Moore’s Last Gasp
Movie: A View to a Kill (1985)
Roger Moore made seven films as 007, appropriately enough, but by the time he filmed his last picture, “A View to a Kill,” he was 57 years old. It’s creepy enough that he romances twenty-something Tanya Roberts (Moore later commented that he learned Robert’s mother was actually older than him). But it went from uncomfortable to downright unsettling when Bond beds the Amazonian henchwoman Mayday, played by Grace Jones. It’s one moment on this list where the actors look to be as embarrassed doing the scene as the audience is watching it.
Timothy Dalton and Maryam D’Abo in ‘The Living Daylights’ (Photo: United Artists/Everett Collection)
007 in Afghanistan
Movie: The Living Daylights (1987)
Maybe this isn’t embarrassing as it is awkward. But in the late ’80s, in the final throes of the Cold War, the Soviet invasion of Afghanistan was big in the news, so it was natural that Bond would get involved. Looking at it now, though, with the U.S. still engaged in its own conflict with Afghan rebels, it’s pretty odd to see 007 joining their ranks.
Pierce Brosnan and Denise Richards in ‘The World Is Not Enough’ (Photo: MGM/Everett Collection)
Christmas? Bah, Humbug!
Movie: The World Is Not Enough (1999)
If you were looking for an actress to play a brilliant, worldly, sophisticate nuclear physicist, truly only one name could possibly jump to your mind: Denise Richards. Yes, the former fashion model and “Wild Things” star was deemed the perfect choice to play the brainy yet unfortunately named Dr. Christmas Jones. Even if Richards were convincing for even a millisecond as a scientist, her “Tomb Raider”-esque outfit of a belly-baring tank top and short shorts would cast doubts that she’d ever be up for a Nobel Prize. Richards, however, did win the Razzie Award for “Worst Supporting Actress.”
Pierce Brosnan in ‘Die Another Day’ (Photo: MGM/Everett Collection)
A Tsunami of Embarrassment
Movie: Die Another Day (2002)
Pierce Brosnan’s fourth and final Bond has plenty of oddities to choose from: Bond with a beard, a bad guy with diamonds embedded in his face, a hotel made entirely of ice, and even an awkward cameo from Madonna. And while some fans will argue vehemently that 007’s invisible car is the most ridiculous moment of this or any other Bond film, there is an even more laughable moment. With a glacier collapsing below him, James Bond kite-surfs a tidal wave. He kite-surfs a tidal wave. Even Brosnan broke down in a laughing fit recalling the scene in the recent Bond documentary “Everything or Nothing.”