Actor Sean Connery is one of the most venerable and versatile actors of the 20th century. Having recently 90, he'll forever be synonymous as the first to play Ian Fleming's agent 007 James Bond. Though it's been nearly 40 years since he played the character on screen, Connery carved quite a career for himself on the big screen with some of his most memorable roles at the toward the turn of the century. Here are why Time Bandits, Highlander, The Untouchables, Indiana Jones and the Last Crusade, and Finding Forrester are my top five Connery films outside of the Bond franchise. Honorable mention goes to Zardoz (1974). The Rock (1996), Entrapment (1999), and The Hunt for Red October (1990).
Time Bandits (1981)
Time Bandits is Terry Gilliam's second feature film after his debut in Jabberwocky (1977). The first of his "Trilogy of Imagination," Gilliam was predominantly known for his animated shorts that tied between skits on Monty Python's Flying Circus on the BBC. With the success of the series, Gilliam occasionally branched out and with fellow Pythons Michael Palin (who co-wrote the film) and John Cleese on the adventure fantasy. The plot follows a group of dwarves who serve God and stumble upon a map where all the time portals are and go exploring. Among their first stops is to the home of a 10-year old boy named Kevin (Craig Warnock). The film features an all-star cast including an appearance by Connery as King Agamemnon of Greece. The film came out at a time when Connery loved the business so much, money became of a little object when he read the script. Originally, Gilliam and Palin looked for an actor who shared the Scottish actor's physical features but was shocked to find Connery took it upon himself to get cast. Having such a good time, he also makes a brief cameo at the end. It goes to show even with reduced screen time, Connery's at his best when he has fun. It also wasn't solely dependent on him to sell the film, which is something.
There are numerous films where Connery takes on the mentor role, but none more so than 1986's Highlander. Playing swordsman Ramirez, he trains Connor MacLeod (Christopher Lambert) in the ways of the blade so he can survive with his powers as an immortal. Casting Connery opposite of the up-and-coming Lambert provides the foundation of what made the original film directed by Russell Mulcahy work. Perhaps in certain respects, the pairing worked almost too well, because it didn't seem like Lambert could carry the presence as intended of the franchise as intended as its sequels are often regarded as inferior to the original. When comparing to other films where they take someone else under his wing like in The Rock (1996), Entrapment (1999), The League of Extraordinary Gentlemen (2003) Connery sides better in those films as the more lively swashbuckler than when he's playing the bitter curmudgeon in the latter two films. Don't get me wrong, The Rock and Entrapment are superior films, but Connery shines best in Highlander.
The Untouchables (1987)
In Brian De Palma's The Untouchables, Connery plays Jim Malone, a veteran Chicago police officer and prohibition-era James Gordon, which sick of seeing corruption running rampant helping Elliot Ness (Kevin Cosner) trying to take down the forces of Al Capone (Robert De Niro). Unlike Time Bandits, The Untouchables is more an ensemble piece not segmented in different eras. Connery not only adds to a powerful cast, but his presence and energy also rubs off significantly bringing the best from his co-stars. You can almost make the argument of how Cosner became a better leading man because of the Scottish actor's presence. It certainly didn't work with David Mamet writing the script. It's a shame how Connery isn't in more of these period pieces.
Indiana Jones and the Last Crusade (1989)
In what some regards as the second-best Indiana Jones film of the franchise after Raiders of the Lost Ark (1980), The Last Crusade (1989) takes Indy (Harrison Ford) on his search for his father Henry Jones Sr (Connery) in search for the holy grail, currently under pursuit from the Nazi regime. While a significant amount of the plot involves the chase similar to its 1980's predecessor, the addition of Connery adds the kind of traveling companion Indy never had in terms of physical presence and wit. No offense to Karen Allen, Kate Capshaw, and Ke Huy Quan, but none can hold the candle as far as one who can complement Indy's knowledge and usefulness on an adventure. Despite The Young Indiana Jones Chronicles already endured its run, a Disney+ prequel series about Henry Jones Sr be a step in the right direction if they finish the fifth film in the franchise. Connery's humor, wit, and comedic timing strike all cylinders in the film and remains arguably the best third film of any trilogy in cinema history.
Finding Forrester (2000)
In what's probably Connery's last great film Finding Forrester (2000), he plays reclusive author William Forrester. The actor revealed the inspiration for the role was author J.D. Salinger of "The Catcher in the Rye" fame. The film's drawn comparisons to Good Will Hunting (1997), which coincidentally enough both films were directed by Gus Van Sant. Mike Rich wrote the 2000 film. Forrester befriends Jamal Wallace (Rob Brown), a gifted student-athlete. After a chance meeting, Forrester and Wallace form a bond with one another and Wallace improves his writing. Wallace's school grows suspicious at the improvement accusing the student of plagiarism. The student swore to his oath to the author not to reveal his presence and the truth, which he upholds. The chemistry between the two makes it one of Connery's finest performances and underappreciated films of his career simply due to its limited release. If you enjoyed Good Will Hunting, you'd be doing yourself a disservice missing out on Finding Forrester.