Sean Connery, the first actor to portray James Bond on the big screen and one of the most popular movie stars of the last century, has died, BBC reports. He was 90.

Thomas Sean Connery was born in Edinburgh, Scotland, on Aug. 25, 1930. The son of a cleaning woman and a factory worker, Connery, who started going by his middle name in his youth, had a younger brother, Neil, who would also go on to be an actor. Before turning to acting, he worked as a milkman and then enlisted in the Royal Navy. He’d later receive a medical discharge because of a duodenal ulcer. Athletic in his youth, Connery started bodybuilding when he was 18 and even competed in the 1953 Mr. Universe competition.

It was during his bodybuilding days that a cash-strapped Connery started acting. His first role was in a London production of “South Pacific” in the early ‘50s. Initially cast as a chorus boy, he moved up to a full role as the production went on. Bitten by the acting bug, Connery kept working though success didn’t come easily. While he’d pick up more roles in theater, TV and, eventually, movies, he was still forced to work odd jobs to make ends meet for much of the decade, even working as a babysitter at one point.

It wasn’t until 1962 that he had his breakthrough when he was cast as James Bond in “Dr. No,” the first film adaptation of Ian Fleming’s beloved spy series. Although he was initially hesitant to commit to a franchise, the films would prove to be a massive success and make Connery an international sex symbol. He would go on to play the character six more times in “From Russia with Love” (1963), “Goldfinger” (1964), “Thunderball” (1965), “You Only Live Twice” (1967), “Diamonds Are Forever” (1971) and “Never Say Never Again” (1983). Though the character would be played by five other actors on the big screen, it’s the Scottish actor who is still most associated with the role.

As much of a success as the Bond films were, Connery soon grew tired of the role, once saying “I’d like to kill him.” He had no shortage of success when he left the franchise, though, starring in a number of the biggest films of the next three decades. Though he’d butt heads with his fellow actors, director and producers films like “Time Bandits” (1982), “The Untouchables” (1988), for which he won the Oscar for Best Supporting Actor, “Indiana Jones and the Last Crusade” (1989), “The Hunt for Red October” (1990) and “The Rock” (1996) made sure he became a film icon for more than just his time in a tux.

Despite a career that stretched over five decades, a series of late career flops, and turning down such successes as “The Matrix” and “The Lord of the Rings” trilogy, sped up the actor’s disillusionment with Hollywood, and in 2007, at the age of 77, he decided to retire from acting for good.

Right as his career was about to take off in 1962, Connery wed Australian actress Diane Cilento. They’d divorce 11 years later in 1973, but not before having a son, Jason, who’d go on to become an actor himself. Two years after his split with Cilento, Connery wed Moroccan-French painter Micheline Roquebrune, who he remained married to until his death.

A proud Scot — he had a tattoo that read “Scotland Forever” — Connery was a member of the Scottish National Party, which pushed for the country’s independence from the UK. His political beliefs are rumored to have stopped him from being knighted in 1997 and 1998, though Queen Elizabeth II would eventually bestow the honor upon him in 2000 in his native Edinburgh.