Top 10 gentleman Rogues

Thomas Crown Affair

There is a saying that ‘Crime doesn’t pay’ and it’s one I whole heartedly endorse. On the silver screen or in literature however, we seem to have taken a different view. The gentleman thief has been widely accepted as the hero we secretly cheer for. The fact he is taking advantage of an undeserving wealthy adversary is overlooked as long as he carries out his antics with style and panache. The formula is similar to that other gentleman hero James Bond (from the books at least), fast cars, beautiful women, impeccable style and a penchant for the exclusive, all served up with exquisite taste.

So When the modern gentleman takes time to unwind, how better than watching some of the legendary screen and literary icons take on the most cunning of roles as a gentleman thief.

Simon Templar – Roger Moore (The Saint)

The Saint first appeared in the books Leslie Charteris published between 1928 and 1963. The adventures of the modern day ‘Robin Hood’ detailed the escapades of this dashing gentleman thief with a merciless streak. It was the 1968 TV series with Roger Moore with his white Volvo p1800 that is now synonymous with the character. It is rumored that James Purefoy pick up the Saint role for a new television series to be broadcast later in the year.

  • First appearance: 1928
  • Nationality: British
  • Finest Hour: 1968 series with Roger Moore in the starring role

Henry Gondorf – Paul Newman (The Sting)

After rookie grifter Johnny Hooker (Robert Redford) tracks down veteran flim-flam man Henry Gondorff (Paul Newman) in 1930’s Chicago, the duo plans to fleece a homicidal racketeer (Robert Shaw) through a phony racetrack scam involving a string of double and triple crosses. The Sting picked up seven Academy Awards, including Oscars for Best Picture, Best Directing (George Roy Hill) and Best Original Screenplay (David S. Ward).

  • First appearance: 1973
  • Nationality: American
  • Finest Hour: 1973 The classic poker scene on the train

Danny Ocean – George Clooney (Ocean’s 11)

As much as I adore the original 1960 movie with Frank Sinatra as Danny Ocean and the rest of his Rat pack buddies, it is the 2001 remake with George Clooney that takes earns a place on this top 10 list. The charismatic Ocean pulls the ultimate gentleman’s con over an equally dashing Terry Benedict played by Andy Garcia. I know I have used the trailer from Ocean’s 13 – as a big fan of Al Pacino I couldn’t resist.

  • First appearance: 1960
  • Nationality: American
  • Finest Hour: The battle of wits with ‘The night fox’ in the 2004 Ocean’s 12

Arthur J Raffles – David Niven (Raffles)

Arthur J. Raffles is a character created in the 1890s by E. W. Hornung, a brother-in-law to Arthur Conan Doyle, the creator of Sherlock Holmes. Raffles is, in many ways, a deliberate inversion of Holmes — he is a “gentleman thief,” living in the Albany, a prestigious address in London, playing cricket for the Gentlemen of England and supporting himself by carrying out ingenious burglaries. He is called the “Amateur Cracksman,” and often, at first, differentiates between himself and the “professors” — professional criminals from the lower classes.

  • First appearance: 1890
  • Nationality: British
  • Finest Hour: On stealing a gold cup from the British museum, Raffles posts it to the Queen as a Diamond Jubilee present!

John ‘The Cat’ Robie – Cary Grant (to catch a thief)

John Robie is a one-time cat burglar, now reformed and living a blameless life in a plush villa. When a fresh set of burglaries rocks the Riviera all bearing the hallmark of Robie’s own robberies, he is the natural suspect. Robie sets out to catch the new burglar himself, mainly to prove his innocence. He is aided by an American heiress, who initially is convinced that he is actually guilty. The title of the movie is derived from the proverb “Set a thief to catch a thief”

  • First appearance: 1952
  • Nationality: British
  • Finest Hour: The scene where Robie gets Jessie’s attention, dropping an expensive casino chip down decolletage of French roulette player.

Asene Lupin – Romain Duris (Arsene Lupin)

A contemporary of Sir Arthur Conan Doyle, Maurice Leblanc (1864-1941) was the creator of the character of gentleman thief Arsène Lupin who, in Francophone countries, has enjoyed a popularity as long-lasting and considerable as Sherlock Holmes in the English-speaking world. Arsène Lupin is a literary descendant of Pierre Alexis Ponson du Terrail’s Rocambole. Like him, he is often a force for good, while operating on the wrong side of the law. Those whom Lupin defeats, always with his characteristic Gallic style and panache, are worse villains than him. Lupin is somewhat similar to A. J. Raffles and anticipates characters such as The Saint.

  • First appearance: 1905
  • Nationality: French
  • Finest Hour: The original books are the original and best.

Charlie Croker – Michael Caine (The Italian Job)

No other film could sum up the sixties England better than this film. It shows one of the most popular cars taking part in the best robbery every committed. Charlie Croker is the lovable rogue working for the most gentlemanly Mr Bridger (Noel Coward). The iconic car chase is so memorable, the final scene with it’s great cliff hanger is delightful. Add to that one of Michael Caines most memorable quotes.

  • First appearance: 1969
  • Nationality: British
  • Finest Hour: “You’re only supposed to blow the bloody doors off!” enough said!

The Phantom – The Pink Panther

David Niven is perfectly cast as the gentleman thief ‘The Phantom’ where he pits his wits against the bumbling and conceited French police inspector Clouseau. Clouseau tries to catch The Phantom, a daring jewel thief whose identity and features are unknown – and is acting right under his nose.

  • First appearance: 1963
  • Nationality: British
  • Finest Hour: It is in fact Peter Sellers Clouseau who steals the show in this amazing film.

Simon Demott – Peter O’Tool (How to steal a million)

Nicole’s father, a legendary art collector, lends his prized Cellini Venus to a prestigious Paris museum. Unfortunately, the Venus was *not* sculpted by Cellini but by Nicole’s grandfather. (Her father is a forger as well, but his specialty is paintings.) Before tests can be done which would prove the Venus a fake, Nicole enlists the services of “society burglar” Simon Demott to steal the million dollar statue.

  • First appearance: 1966
  • Nationality: British

Thomas Crowne – Steve McQueen (The Thomas Crowne affair)

A debonair, adventuresome bank executive believes he has pulled off the perfect multi-million dollar heist, only to match wits with a sexy insurance investigator who will do anything to get her man.

  • First appearance: 1963
  • Nationality: American
  • Finest Hour: A slight cheat, but the finale of the 1999 remake was genius.

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