by Alex Castle
“The money’s getting to be out of control now… sometimes, the more money you have, the more blues you can sing,” Jimi Hendrix told Dick Cavett on national TV. Thirty years later, the Notorious B.I.G. was a little more succinct: “Mo’ money, mo’ problems.” We all like to imagine that our problems would be over if we could just get a big check to cover expenses, but it’s not that easy — at least, not in the movies.
This past week Leonardo Dicaprio took on the iconic role of Jay Gatsby, haunted, self-made millionaire in Baz Luhrmann’s The Great Gatsby, pining after a lost love he can never get back. There’s something satisfying about watching the rich have a hard time, and there is no shortage of great movies to prove that point, just a click away on Blockbuster On Demand!
One of Richard Pryor’s best comedies has him as a penniless minor-league pitcher who learns he’s inherited $300 million from a long-lost uncle, on one condition: he has to squander $30 million and leave nothing to show for it. An inventive look at how the rich get rich without even trying, featuring John Candy as Pryor’s best friend.
Alicia Silverstone plays a richer-than-rich girl who spars with her socially conscious ex-stepbrother (Paul Rudd) at home and reigns supreme at school, taking pity on an uncool classmate (Brittany Murphy) with a free makeover and playing matchmaker. Before long her puppet-mastery starts to backfire and she has to reassess. A cult classic.
“I’ll give you one million dollars for a night with your wife,” super-rich Robert Redford offers struggling architect Woody Harrelson, and one of the most talked-about movies of the ’90s is underway. What is it about happily married Demi Moore that prompts this offer? Should they take it? If they do, then what? Directed by Adrian Lyne, the master of upperclass ennui (Unfaithful, Fatal Attraction).
Matt Damon showed the world that he was for real with his performance as a chameleonic con man slithering his way into the jet set, specifically shipping heir Dickie Greenleaf (Jude Law) and his girlfriend Marge (Gwyneth Paltrow). Beautifully shot in Italy and set in the late ’50s for extra flavor.
Whether you prefer the 1981 original or the 2011 remake (we’re partial to the original), the story is pretty much the same: a spoiled-rotten playboy (Dudley Moore or Russell Brand) who spends more time drunk than sober meets a delightful, less fortunate young lady (Liza Minnelli or Greta Gerwig), complicating his upcoming arranged marriage. The remake is not terrible, but the original is really charming, particularly the scenes between Dudley Moore and John Gielgud as his butler.
The world fell in love with Audrey Hepburn in this light romantic comedy about a princess, isolated from the outside world by her royal handlers, who slips security to take in the sights of Rome on her own, where she meets a journalist (Gregory Peck) who becomes her tour guide. Hepburn is absolutely adorable in the role.
Kajillionaire investment banker Richard Gere is about to sell his company for hundreds of millions, but he has a couple of problems: one, he accidentally crashed his car and killed his mistress, and two, a past deal has gone south and he’s way overleveraged. A tight, tense thriller with great supporting turns by Susan Sarandon and Brit Marling.
What kind of gift do you get the man who has everything? For his birthday, super-rich Michael Douglas gets an unusual gift from his brother (Sean Penn): a totally immersive ‘game’ played all over the city, pushing Douglas to defend his wealth and get to the bottom of what’s happening. David Fincher lends his characteristic dread, dark directing style.
The last time Hollywood took on the original Great American Novel, Robert Redford played the title role and Mia Farrow was the object of his quixotic desire. This was an unusually expensive production for the time, and it shows on the screen. The script was written by Francis Ford Coppola and Truman Capote, and is faithful to the book in skewering the strange world of the idle rich.