If you haven’t yet watched Ben Stiller’s 1987 trailer, The Hustler of Money, a parody of Martin Scorsese’s 1986 film The Color of Money, stop whatever you’re doing, watch the video below, and spend the next 5 minutes doubled-over in gut-busting laughter. It’s that good.
Starring Ben Stiller (as Tom Cruise playing “Wince”) and Frasier’s John Mahoney (as Paul Newman playing “Fast” Eddie Felson), the trailer is for a film in which Tom Cruise plays a cocky but immensely talented bowler, who struts around the bowling lanes in a black “WINCE” t-shirt (itself, a mockery of the “VINCE” t-shirt Cruise wears in the film) with his slicked-black hair and perpetual ear-to-ear grimace, as he palms bowling balls and throws strikes with two balls simultaneously. As Tom Cruise did in the original film, Wince challenges anyone to a game, including a group of octogenarians on walkers, when he is not otherwise slobbering all over his girlfriend. Eric Clapton’s “It’s in the Way That You Use It,” a song written for and memorably used in the opening scene of the original The Color of Money, plays in the background.
Eddie, after failing to peddle Newman’s Own salad dressing to the bowling hall’s bartender (played by Ben Stiller’s real-life mother Anne Meara) takes an interest in Wince after seeing the “kid nail a 7-10 split.” He agrees to teach Wince how to hustle in bowling, prompting a very funny spoof of the original dialogue about having the “flake down cold, but can he turn it on and off.”
With Warren Zevon’s “Werewolves of London” playing in the background (the song famously used in The Color of Money’s “Doom” hustling scene), we watch Wince maneuver through a series of struts, dribbles, juggles, and throws, as he hustles local bowling patrons, including a young boy, mothered by Julie Hagerty (from Airplane). Meanwhile, Eddie attempts to regain his bowling mojo, but breaks down after losing his bowling shoes, putting on an over-the-top display of sadness, blatantly designed to con the Academy of Motion Pictures Arts and Sciences into giving Newman an award. The trailer ends by lampooning the final scene of The Color of Money, but in this case, it’s with Eddie throwing a bowling ball and then screaming “My back!” (rather than “I’m back!”).
Ben Stiller made The Hustler of Money when he was just 22. At the time, he was working on Broadway. Having worked with John Mahoney on a satirical mockumentary, he followed it up with The Hustler of Money parody, which was picked up by Saturday Night Live and aired later that year. Interestingly, SNL offered Stiller a job as a writer and actor two years later, but he quit after appearing on only four episodes.
While The Hustler of Money was the first time Stiller portrayed Cruise, it was not the last. He portrayed Cruise on The Ben Stiller Show as part of a “Dress Casual” skit. Then, for the 2000 MTV Video Awards, Stiller and Cruise joined forces in one of the best parodies of all time (shown below), with Stiller playing Tom Crooze, the stunt double for Tom Cruise, in Mission: Impossible. In 2008, they teamed up in the Stiller-directed comedy Tropic Thunder. And, they are allegedly working together on the development of The Hardy Men, an updated version of “The Hardy Boys,” suggesting more great laughs could be coming soon.
