Since the early days of his career, Michael Caine has been synonymous with the heist genre, often playing charming thieves that the audience can easily root for. Starting with early hits likeGambitandThe Italian Job,many ofMichael Caine’s best moviesfeatured heists. He’s often one of the thieves, but he’s also played some great villains over the years.

Caine has starred in some of thebest heist moviesof all time, and his history with the genre charts its evolution. From the stylish capers of the 1960s, through more violent thrillers in the 1970s and 1980s to the current crop of comedies which deconstruct the form, Caine has been there. Not many actors have been in so many excellent heist movies.

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Going in Styleis a remake of a 1979 heist movie starring comedy legends George Burns and Art Carney. Zach Braff takes on directorial duties, although it’s a different kind of movie to his indie comedy-dramas. The story revolves around three old friends who decide to rob a bank when their pensions are taken away from them. This gives it a sly anti-establishment stance, as the friends channel their rage at the financial institutions that have wronged them.

Going in Styleambles from breezy, character-based humor to wry deconstructions of the heist genre.

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Going in Styleshares a lot in common with another Michael Caine heist movie,King of Thieves,as both movies follow a group of pensioners turning to crime. However,King of Thievesis based on a true story, andGoing in Styledoesn’t have any such restrictions. This means that it can amble from breezy, character-based humor to wry deconstructions of the heist genre.Caine ensures that the caper is always charming, along with Alan Arkin and Morgan Freeman.

Harry and Walter Go to New Yorktakes place in the late 19th century, as two dim-witted con men try to leave their life as vaudeville performers behind by making the move to robbing banks. Diane Keaton and James Caan have aGodfatherreunion of sorts while Elliott Gould is as hilarious as ever playing the more frantic and outgoing of the two wannabe robbers. Michael Caine plays his part as the slimy professional thief perfectly.

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Michael Caine’s character, Adam Worth, was a real-life mob boss and thief, although the story ofHarry and Walter Go to New Yorkis otherwise entirely fictional.

Caine always seems to enjoy himself when he gets the chance to play a villain, andHarry and Walter Go to New Yorkis no different. Adam Worth often towers over the two pretenders to his throne, sneering down at them as he enjoys a life of luxury, even when he’s behind bars.He’s a charming villain who adds an extra spark to the drama. He’s also the perfect comedic foil to the two inept, inexperienced heroes.

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Now You See Mestarts with the simple premise that a group of stage magicians use their skills to pull elaborate heists, and it pushes this idea near its breaking point. The concept allowsNow You See Meto deliver more off-the-wall spectacle than many other crime movies, partly because many of the most impressive tricks are never explained.Whether some magic is actually real inNow You See Meis still up for debate.

Now You See Me 3’s Best Trick Would Be Bringing This Acting Legend Out Of Retirement

Now You See Me 3 is bringing back a lot of characters from the first two, and there is one key cast member who should show up even if for a cameo.

Michael Caine plays the benefactor of the Four Horsemen inNow You See Me,but he quickly morphs into a villain as the magicians reject his tainted money and embark on a Robin Hood-style campaign to expose corruption and corporate greed. Caine also makes a brief appearance in the sequel, but he won’t be in the long-awaitedNow You See Me 3following his retirement from acting.

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AlthoughThe Italian Jobgot an American remake in 2003, it’s hard to replicate the sheer entertainment value of the original. Michael Caine stars as the leader of a group of brash young thieves who tear through the picturesque streets of Turin to steal a large delivery of gold bullion. The thieves aren’t the typical heist movie types. Instead, their jovial antics and excessive drinking make them look more like a group of English football hooligans.

Michael Caine puts his cockney charms to good use, offering the perfect blend of suave, deadpan wit and imposing volatility.

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The Italian Jobopens with a gorgeous ballad sung by Matt Monro, and this sets the tone for a stylish heist movie. Michael Caine puts his cockney charms to good use, offering the perfect blend of suave, deadpan wit and imposing volatility.TheItalian Job’s cliffhanger endingis the perfect capper to a frenzied criminal narrative, and it lets the audience decide for themselves whether the lovable rogues get away with it all in the end.

Gambitwas one of Michael Caine’s earliest hits, and it remains his very best heist movie. He stars as a dapper thief who recruits a dancer to assist him in his most ambitious heist yet, purely because she looks just like his mark’s deceased wife. This sets up a hilarious romantic comedy, in which the thief’s assumptions are torn to shreds by his rambunctious new accomplice.

Gambit’s tagline, “Go ahead, tell the end. But please don’t tell the beginning!” hints toward its unusual structure. To explain it in detail would be to spoil the movie’s greatest joy, but it’s worth saying thatfew movies have ever attempted a subversive twist quite as bold and unexpectedasGambit.Putting the structure and the boisterous comedy to one side,Gambit’s infectious swagger is emblematic of the prevailing style ofheist movies in the 1960s, and it’s still a riot almost 60 years later.