Michael Caine’s 5 Best Heist Movies, Ranked

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 like Gambit and The Italian Job, many of Michael Caine’s best movies featured 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 the best heist movies of 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.

5

Going In Style (2017)

Michael Caine’s Late-Career Heist Movie Remake Parodies His Earlier Roles

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Going in Style

PG-13

Comedy

Crime

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4/10

Release Date

April 7, 2017

Runtime

96 Minutes

Director

Zach Braff

Writers

Theodore Melfi

Cast

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

Going in Style shares 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 Thieves is based on a true story, and Going in Style doesn’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.

4

Harry & Walter Go To New York (1976)

Caine Plays The Villain In A Period Crime Comedy

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Harry and Walter Go to New York

PG

Crime

Comedy

Release Date

June 17, 1976

Runtime

115 minutes

Director

Mark Rydell

Writers

John Byrum

Producers

Don Devlin, Harry Gittes

Cast

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Harry and Walter Go to New York takes 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 a Godfather reunion 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.

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

Caine always seems to enjoy himself when he gets the chance to play a villain, and Harry and Walter Go to New York is 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.

3

Now You See Me (2013)

Caine Helped The Now You See Me Franchise Get Started

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Now You See Me

PG-13

Mystery

Thriller

Crime

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7/10

9/10

Release Date

May 31, 2013

Runtime

115 minutes

Director

Louis Leterrier

Writers

Ed Solomon, Edward Ricourt, Boaz Yakin

Sequel(s)

Now You See Me 2, Now You See Me 3

Cast

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Now You See Me starts 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 allows Now You See Me to 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 in Now You See Me is still up for debate.

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Michael Caine plays the benefactor of the Four Horsemen in Now 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-awaited Now You See Me 3 following his retirement from acting.

2

The Italian Job (1969)

Caine’s Dry Wit Plays Off His Supporting Cast Perfectly

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The Italian Job

G

Crime

Action

Comedy

Release Date

September 3, 1969

Runtime

99 Minutes

Director

Peter Collinson

Writers

Troy Kennedy Martin

Producers

Michael Deeley

Cast

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  • Shot Of Michael Caine In The World premiere of 'The Great Escaper' at BFI Southbank

    Michael Caine

    Charlie Croker

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    Noël Coward

    Mr. Bridger

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    Benny Hill

    Professor Simon Peach

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    Raf Vallone

    Lorna

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Although The Italian Job got 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.

The Italian Job opens 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. The Italian Job‘s cliffhanger ending is 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.

1

Gambit (1966)

Michael Caine And Shirley MacLaine Make The Perfect Pair

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Gambit

NR

Comedy

Crime

Release Date

December 21, 1966

Runtime

109 minutes

Director

Ronald Neame

Writers

Alvin Sargent

Producers

Léo L. Fuchs

Cast

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  • Shot Of Michael Caine In The World premiere of 'The Great Escaper' at BFI Southbank

    Michael Caine

    Harry

  • Headshot Of Shirley MacLaine

    Shirley MacLaine

    Nicole

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    Herbert Lom

    Shahbandar

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    Roger C. Carmel

    Ram

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Gambit was 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 that few movies have ever attempted a subversive twist quite as bold and unexpected as Gambit. Putting the structure and the boisterous comedy to one side, Gambit‘s infectious swagger is emblematic of the prevailing style of heist movies in the 1960s, and it’s still a riot almost 60 years later.