Connery's breakthrough came in the role of secret agent James Bond. He played the character in the first five Bond films: Dr. No (1962), From Russia with Love (1963), Goldfinger (1964), Thunderball (1965), and You Only Live Twice (1967) -- then appeared again as Bond in Diamonds Are Forever (1971) and Never Say Never Again (1983). All seven films were commercially successful.
James Bond's creator, Ian Fleming, originally doubted Connery's casting, saying, "He's not what I envisioned of James Bond looks" and "I’m looking for Commander Bond and not an overgrown stunt-man," adding that Connery (muscular, 6' 2", and a Scot) was unrefined. However, Fleming's girlfriend told him Connery had the requisite sexual charisma. Fleming changed his mind after the successful Dr. No premiere; he was so impressed, he created a half-Scottish, half-Swiss heritage for the literary James Bond in the later novels.
Connery's portrayal of Bond owes much to stylistic tutelage from director Terence Young, polishing the actor while using his physical grace and presence for the action. Robert Cotton wrote in one Connery biography that Lois Maxwell (the first Miss Moneypenny) noticed, "Terence took Sean under his wing. He took him to dinner, showed him how to walk, how to talk, even how to eat." Cotton wrote, "Some cast members remarked that Connery was simply doing a Terence Young impression, but Young and Connery knew they were on the right track."
In 2005, From Russia with Love was adapted by Electronic Arts into a video game, titled James Bond 007: From Russia with Love, which featured all-new voice work by Connery as well as his likeness, and those of several of the film's supporting cast.