1. "The Thomas Crown Affair" (1968)
What happens when a dashing millionaire bored out of his mind plans a bank heist just for the thrill of it? Enter Thomas Crown, who does just that. Hiring professionals, he orchestrates the perfect crime without ever getting his hands dirty.
But here comes the catch: an equally sharp insurance investigator, Vicky Anderson, gets onto his trail. Box office-wise, it didn't break records, but it sure did break the mold. With its split-screen style, you'll see the '60s like never before.
2. "Gambit" (1966)
How about a plot to steal a priceless statue with the help of a showgirl who's a dead ringer for the widowed owner's late wife? Sounds intriguing, right? Harry Dean, the mastermind, recruits Nicole Chang, the doppelganger, for this eccentric plan.
The idea? Use Nicole as a distraction while he takes the prize. Easy? Think again! As plans go awry and unforeseen hitches emerge, you might find yourself asking, "Can they even pull this off?"
3. "The Italian Job" (1969)
The name's a dead giveaway, isn't it? Set in Italy with Mini Coopers, gold bullion, and Michael Caine? Get ready for a ride. Charlie Croker, fresh out of prison, inherits a plan to steal gold in the middle of Turin's traffic chaos.
With the mafia and the police on their tails, the gang relies on three Mini Coopers to make their speedy escape. What follows is a chase sequence to rival the best of them. Oh, and that cliffhanger ending? You'll be hanging onto your seat!
4. "Dead Heat on a Merry-Go-Round" (1966)
The criminally underrated James Coburn plays Eli Kotch, a con artist who's always one step ahead. Released from prison early (because of his silver tongue, of course!), he's got a plan. The target? A bank at Los Angeles International Airport.
The plan involves seduction, deceit, and playing roles ranging from a German psychiatrist to a film producer. Just a day's work for Eli!
5. "The Pink Panther" (1963)
Oh, Inspector Jacques Clouseau, how do we count the laughs you've given us? In this flick, Clouseau is after the notorious Phantom, a jewel thief, before he can nab the famous Pink Panther diamond. But the bumbling detective doesn't realize his own wife is the Phantom's girl and helps in his crimes.
Hijinks, hilarity, and, let's face it, a whole lot of second-hand embarrassment ensue. But that's what makes it so brilliant! It spawned numerous sequels, but if you ask me, the original caper is pure gold. It did okay in the box office, but its slapstick humor was a tad too advanced for its time.
6. "How to Steal a Million" (1966)
Audrey Hepburn and Peter O'Toole in a comedy about stealing a sculpture? Say no more! Hepburn plays Nicole, the daughter of an art forger. When her father's Cellini Venus statue is insured for a million bucks and set to be examined by experts, panic ensues.
Enter Simon Dermott (O'Toole), a burglar she meets while he's robbing her mansion (yep, you read that right). The duo hatches a plan to steal the statue before its secret is unveiled.
7. "Topkapi" (1964)
When a small-time con-woman and her ex-lover scheme to steal a jeweled dagger from the Topkapi Museum in Istanbul, what could go wrong? Well, lots.
The plot thickens as they assemble a team, including a mute acrobat, to assist. Yet, the real challenge? Evading the vigilant eyes of the local police inspector, who's a tad suspicious. The entire heist sequence, carried out in utter silence, is a masterclass in tension and comedy.
8. "Two-Way Stretch" (1960)
Ever heard of inmates breaking into a prison? No? Well, let Peter Sellers introduce you to the concept. Dodger Lane, sentenced to the slammer, finds out about a stash of diamonds that are up for grabs.
The plan? Break out of prison, nab the diamonds, and then sneak back in before morning roll call. With the perfect alibi (they were in prison!), it's the perfect crime. Or is it?
9. "The Wrong Box" (1966)
In Victorian England, a tontine is established for a dozen children. The last surviving member would get the fortune. Flash forward, two elderly brothers remain. When one mistakenly believes the other's dead, a series of comedic blunders ensues.
hrow in Michael Caine and Peter Cook as bumbling relatives, hoping to cash in, and you've got yourself a party.
10. "The Jokers" (1967)
Two brothers, tired of the system, plan to steal the crown jewels. Not for the riches, but for the thrill of it. Michael (Michael Crawford) and David (Oliver Reed) Tremayne want to make a point and showcase the vulnerabilities of the establishment. Their audacious plot and the establishment's clumsy attempts to thwart them create a delightful mix of satire and thrill.