- Of the six actors who have played James Bond, he is the only one who, like Bond, served in the Royal Navy.
- Terry Gilliam did not intend to cast him as King Agamemnon in Time Bandits (1981), he simply wrote in the screenplay that when Agamemnon took off his helmet he looked "exactly like Sean Connery." To Gilliam's surprise, the script found its way into Connery's hands and Connery subsequently expressed interest in doing the film.
- He was once stopped for speeding by an officer named Sergeant James Bond.
- He was paid a huge sum to return as James Bond for Diamonds Are Forever (1971), setting a record. It was donated to his Scottish charity.
- He donated his salary from Robin Hood: Prince of Thieves (1991) to charity.
- He said in an interview that during the filming of Never Say Never Again (1983), he was taking martial arts lessons and in the process angered the instructor who in turn broke his wrist. Connery stayed with the wrist broken for a number of years thinking it was only a minor pain... the instructor was Steven Seagal.
- His favorite Bond film is From Russia with Love (1963).
- He wore a toupee in his movies from "Dr No" on, as he started losing his hair at 17. Various techniques were used to make the most of the hair he still did have for other roles, and he began wearing a hairpiece in 1958.
- He had a difficult time getting work after he abandoned the James Bond role a second time after Diamonds Are Forever (1971) for which he received a record salary. Director John Boorman thus was able to hire him very cheaply for his low-budget production of Zardoz (1974).
- He turned down the role of Gandalf in The Lord of the Rings series (The Lord of the Rings: The Fellowship of the Ring (2001), The Lord of the Rings: The Two Towers (2002), and The Lord of the Rings: The Return of the King (2003)) because he didn't want to film down in New Zealand for 18 months, and could not understand the novels. The decision not to appear in the trilogy cost the actor an estimated $450 million.
- He has two small tattoos on his right arm. One says "Scotland forever", the other "Mum and Dad." He got them when he enlisted in the Royal Navy at the age of 16.
- He turned down the title role in the original The Thomas Crown Affair (1968), which he later admitted was a huge mistake on his part.
- He formerly worked as a coffin polisher.
- He turned down the role of Simon Gruber in Die Hard with a Vengeance (1995) due to the diabolical nature of the character. Director John McTiernan, who directed Connery in The Hunt for Red October (1990) and Medicine Man (1992), said he was the very first choice for that role.
- He was delighted to be honored with the American Film Institute's Lifetime Achievement Award, which he will receive on June 8 2006 in Los Angeles, as he was honored despite his reputation as a harsh critic of the movie industry. "It means a tremendous amount, especially because of some of the things I have said about Hollywood.".
- He improvised his iconic line "Bond. James Bond" in Dr No (1962) after finding that the initial introduction line "I am James Bond" was flat and sounded unnatural. It took a few subsequent takes before he included the pause, giving the line it's effect.
- During his time as a milkman, Connery delivered to Fettes School in Edinburgh - the same school which James Bond attended in Ian Fleming's novels following his expulsion from Eton.
- After his service with the Merchant Navy, he worked as a nude model for Edinburgh art students.
- He was involved with Jill St. John and Lana Wood at the same time while filming Diamonds Are Forever (1971).
- The role of Mufasa in The Lion King (1994) was written with him in mind.
- He turned down the role of John Hammond in Jurassic Park (1993). Coincidentally, his Indiana Jones and the Last Crusade (1989) co-star, Harrison Ford, was offered the role of Dr. Alan Grant. Not to mention, it would've reunited both of them with director Steven Spielberg.
- Ian Fleming, the creator of James Bond, originally did not like him being cast as Bond for Dr. No (1962) because he felt that he was too "unrefined". The actor whom Fleming embodied Bond in Fleming's mind was Cary Grant. Fleming later changed his mind and admitted he was ideally cast in the role.
- He was presented with the American Film Institute's Lifetime Achievement Award by his Indiana Jones and the Last Crusade (1989) co-star Harrison Ford, who told him, "John Wayne gave us the old West. James Stewart gave us our town. You gave us the world." (8 June 2006).
- He was almost killed filming the helicopter chase scene in From Russia with Love (1963) when the inexperienced helicopter pilot flew in too close and almost decapitated him.
- He joined the Merchant Navy as a teenager but stomach ulcers forced him to leave. He received a disability pension for a period after this.
- He and his wife are living in the Bahamas. (May 2008)
- His father Joseph was of half Irish and half Scottish descent, and his mother Euphemia was of Scottish ancestry.
- He was the original choice to play Sybock in Star Trek V: The Final Frontier (1989), but he was busy with Indiana Jones and the Last Crusade (1989). The words in the film "Sha Ka Ree" are a play on his name.
- If Never Say Never Again (1983) can be included as an official 007 installment, then Connery ties with Roger Moore for the most portrayals of James Bond - a total of 7 each. Otherwise Moore holds the record.
- Of his career choices in the '90s (pretty much his last decade in film), The Rock (1996) and Entrapment (1999) are the films he liked the most. On the other hand, The Avengers (1998) was a film he regretted doing at all.
- He won the role of James Bond after producer Albert R. Broccoli attended a screening of Sean in Darby O'Gill and the Little People (1959). He was particularly impressed with the fistfight Sean has with a village bully at the climax of the film. Cubby later had his wife, writer Dana Broccoli, see the film and she confirmed his sex appeal.
- He once worked as a bricklayer.
- He brought future James Bond, Roger Moore to a press screening in Paris for Diamonds Are Forever (1971).
- He had radiation therapy for an undisclosed throat ailment in 1993. In a February 1995 interview with Entertainment Weekly, Connery said the treatment had been to remove benign tumors from his vocal chords after he found himself losing his voice while filming Rising Sun (1993).
- He announced his retirement in an interview in New York City during the Tartan Week 2006 celebrations. "I have retired for good," he said.
- He has his own film production company (Fountainbridge Films). Fountainbridge is an area of Edinburgh where he was born.
- Tippi Hedren, his leading lady from Marnie (1964), devoted a full page of photographs on him in her memoir "Tippi" (2016). She wrote that she was stunned that her director Alfred Hitchcock had cast the sexiest man alive to play opposite her, since she was supposed to play a frigid woman in the film. She asked Hitchcock how she can play such a role, when the iciest of women would melt in Sean's presence. He told her "It's called acting, my dear." He did order Sean not to touch her, just as he had ordered Rod Taylor not to touch her during The Birds (1963). Many people have asked her whether she had an affair with Sean after seeing their amazing onscreen chemistry, and she said she didn't, because she was too dedicated to acting, but joked that she later regretted her decision. In 2006, she met with Sean when he was awarded the AFI Lifetime Achievement Award. He kissed her on the cheek sweetly and mentioned how he wasn't allowed to do that on the set of Marnie (1964). In 2017, she told "The Hollywood Reporter" and her daughter Melanie Griffith, granddaughter Dakota Johnson and Dakota's father Don Johnson that Sean was her first celebrity crush. Their friendship lasted more than 50 years, since they still keep in touch, even though they live on different continents.
- He regards the character he played in The Man Who Would Be King (1975) as his favorite movie role.
- He formerly worked as a milk delivery man.
- Connery and Albert R. Broccoli were on bad terms after he left the series. He declined to attend Broccoli's funeral.
- He had cataracts removed from both eyes in 2003.
- He underwent surgery at a New York hospital to remove a tumor from his kidney in January 2006. Connery's brother Neil said, "As far as I'm led to believe the tumor was benign. He seems to be quite upbeat about it.".
- He started smoking when he was nine years old.
- He pulled out of a seven-figure deal for a planned autobiography for the second time, in March 2005. The actor signed a deal in 2004 with ghostwriter Hunter Davies to produce an account of his life from Edinburgh milkman to international film superstar. Six months prior to his hook-up with Davies, Connery also canceled a similar deal with Scottish writer Meg Henderson, who said later: "He isn't the man I thought he was.".
- He once went to the Paramount Executive commissary, which was filled with A-list celebrities and executives. When he walked in, the room went silent, to which he simply quipped "Oh, eat your lunch".
- In 1953, he entered the Mr. Universe contest, finishing third in the tall man's division.
- Harry Saltzman and Albert R. Broccoli, the original producers of the James Bond films, cast him because they liked how he was a big, tough-looking man who nonetheless moved gracefully ("like a cat").
- Connery received excellent notices for his starring role in Macbeth (1961) and longed to make a film of "The Scottish Play." His plans for a film in the early 1970s were terminated by the production of Roman Polanski's Macbeth (1971).
- He once appeared in a BBC advertisement stating he was anti-gun, and in 1999 he called on the Scottish parliament to ban all handguns in the country. When he found out that members of the National Rifle Association in America had blacklisted him as a star to boycott, Connery said he was more than happy to be on their list.
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