To get one fact immediately out of the way: it's not a mystery. Sean Connery effectively announced his retirement in a 2005 interview with The Scotsman, explaining he was "fed up with the idiots...the ever-widening gap between people who know how to make movies and the people who green-light the movies." Of course, this was on the heels of The League of Extraordinary Gentleman, his last film role and an all-around critical and box office failure, but we'll forget about that for a moment.
The real question is, when did the dashing actor's career start going downhill? I would argue that he peaked in the late 80's - early 90's before nosediving right after The Rock in 1996. After that film (which was more of a career saver for Nicolas Cage than anything else), Sir Connery was in only five more films: The Avengers, Playing By Heart, Entrapment, Finding Forrester, and, of course, the aforementioned LXG. Not the smooth exit we might have expected from the original James Bond.
But aside from six Bond films and a Supporting Actor Oscar win in The Untouchables, could you make a case that Connery really had an impressive film career in the first place? His classic looks and oft-imitated Scottish brogue made him an iconic figure in Hollywood, but he's not regarded as the best actor of his generation or anything, right? In fact, take away his memorable roles in Highlander, Indiana Jones and the Last Crusade, The Hunt for Red October, Robin Hood: Prince of Thieves, and Medicine Man, and Connery doesn't have many post-Bond credits worth mentioning. If it wasn't for 007, he might have just been known as another bodybuilder turned actor. (I'm almost tempted to question the 2007 Lifetime Achievement Award he received from the American Film Institute, placing him in the company of some of the most influential Hollywood figures in history). But he was Bond, and that might have made all the difference. That and the fact that women find him disarmingly attractive, "for an older guy."
Since his retirement Connery, now 78, has remained mostly quiet, persevering through several health problems and campaigning for Scottish independence from the UK, despite his acceptance of the British knighthood in 2000. I can't really put my finger on why, but I'm a little puzzled by the purpose of his official website (not to be confused with www.yourethemannowdog.com). If he's trying to remain relevant he might want to try to cash in on more SNL skits, but I have to say, the website's "Spot the Young Connery" game is kind of fun - for one play.
Doesn't anybody in Hollywood have one last good role for Sean Connery?