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Viewer Guide: “The Thomas Crown Affair” and “Jack Goes Boating”

May 16, 2022 | Richard Peña


The Thomas Crown Affair (1968).

This week’s double feature begins with The Thomas Crown Affair, the 1968 crime caper directed by Norman Jewison. 

Steve McQueen stars in the title role as a suave but bored multi-millionaire with a daredevil streak, whose restlessness leads him to dabble in the riskiest kind of high stakes adventure: bank robbery. Engineering the perfect heist from his stylish Boston office, Crown disguises his identity with his five accomplices, and calls in his instructions to them on variety of public pay phones. Successfully masterminding a heist that nets him over $2.6 million, Crown laughs all the way to his Swiss bank, leaving the Boston police and insurance investigators fuming in mutual recrimination. Enter Faye Dunaway as Vicki Anderson, an unorthodox new breed of insurance investigator—and the epitome of 60s high fashion in her 29 costume changes. Motivated by the 10% fee she receives for any recovered money, Vicki has a hunch that Thomas just might be her man—in more ways than one. And so begins a most unusual cat and mouse game, with the cat and the mouse freely discussing their adversarial relationship as they embark on a whirlwind affair, all set to Michel Legrand’s swinging soundtrack and Oscar-winning theme song, “The Windmills of Your Mind.” 

Having starred in a string of action movies, Steve McQueen was eager to play against type in a more debonair role. After directing McQueen in The Cincinnati Kid, Norman Jewison found the perfect vehicle for him in a debut screenplay by lawyer Alan Trustman, who had once worked at the First National Bank of Boston—and daydreamed about how to rob it. Despite its sophisticated settings, The Thomas Crown Affair still allowed McQueen to retain his trademark anti-authoritarian cool, as well as indulge in favorite pastimes like drag racing in the dune buggy sequence. Jewison reportedly cast Faye Dunaway after screening footage of her breakout performance in Bonnie and Clyde before its release. The bank robbery sequence was shot with hidden cameras, and while bank officials and guards were aware everything was staged, some unsuspecting passersby were not. Perhaps it was because their big screen kiss required eight hours to film, but both McQueen and Dunaway called the movie a personal favorite. In 1999, Dunaway returned for a cameo role in the remake starring Pierce Brosnan and Rene Russo, which transferred the bank heist plot to an art theft at the Metropolitan Museum of Art. 


Jack Goes Boating (2010).

This week’s indie is Jack Goes Boating, a 2010 offbeat romantic comedy-drama marking the directorial debut of Philip Seymour Hoffman. 

In addition to directing, Philip Seymour Hoffman stars in the title role, playing a New York City limo driver working for his Uncle Frank. A gentle, soft-spoken bear of a guy whose life seems to have stalled out in his early forties, Jack has become something of a project for his fellow limo driver and friend Clyde, played by John Ortiz. Clyde is determined to set Frank up with Connie, played by Amy Ryan, a co-worker friend of his wife Lucy, played by Daphne Rubin-Vega. Connie works with Lucy at an upscale funeral home, and like Jack, seems adrift as well, still in a tender emotional state after the death of her parents. When a flicker of romance seems to kindle between Jack and Connie, Clyde and Lucy encourage Jack to embark on a campaign of self-improvement, including learning how to swim in order to take Connie boating in Central Park in the spring, as well as cooking gourmet home dinners and breaking out of his career stagnation with a new job at the MTA. But as Jack dutifully follows Clyde and Lucy’s tutelage, he starts to notice cracks in his mentors’ marriage, observing the stresses that come with the territory in any longtime relationship. If Clyde and Lucy are examples of married life, is that a “goal” that Jack really wants to pursue? 

Originating in 2007 as an Off-Broadway play by Robert Glaudini, Jack Goes Boating was a production of the LAByrinth Theater Company, which was jointly led by Philip Seymour Hoffman and John Ortiz during its first decade. With a story reminiscent of Marty, Paddy Chayefsky’s midcentury drama of two middle-aged Manhattanites finally finding romance, the film at times recalls the naturalistic dramas of British writer-director Mike Leigh. With Hoffman reprising his stage role for the film along with fellow cast members John Ortiz and Daphne Rubin-Vega, Amy Ryan joined the production in the expanded role of Connie. An accomplished theater director, Hoffman initially had no interest in directing the film himself, but ultimately accepted the job at the urging of Ortiz. Although enjoying the experience of movie directing, Hoffman was not a fan of having to direct himself. Premiering at the 2010 Sundance Film Festival, the film sadly represents Philip Seymour Hoffman’s sole film directing credit before his untimely death at the age of 46 in 2014. 

Richard Peña is a Professor of Film Studies at Columbia University, where he specializes in film theory and international cinema.  

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