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Along with The Sting, Paper Moon, made a few years earlier, may be the quintessential Depression-era conman film. But while The Sting, though terrific, was more of a gimmicky star vehicle, Paper Moon has even more heart than con. In the best role of his career, Ryan O’Neal (once upon a time he was actually a superstar) stars opposite his real-life daughter Tatum O’Neal. At just eight-years-old, she gives one of the most acclaimed child performances ever. Director Peter Bogdanovich was working at the peak of his powers, fresh off the brilliant The Last Picture Show and the popular What’s Up, Doc? He vividly recreates the flat, lonely landscapes of 1930s Kansas; shooting in beautiful black & white, the period detail is as good as any modern film has ever done.

Paper Moon is based on the novel Addie Pray by Joe David Brown (Kings Go Forth), with the screenplay by Alvin Sargent, whose massive screenwriting career ranges from Ordinary People to the recent Spider-Man sequels. Moses Pray (Ryan) is a two-bit conman. He thinks he can make a buck when, after the funeral of a one-time lover, he agrees to accompany the woman’s eight-year-old orphaned daughter, Addie (Tatum), to the train station where she will be shipped off to a distant family. She realizes that he has scammed her out of her inheritance money, so to pay him back the two end up joining up on a cross-country con job.  At first they’re at odds but eventually Moses comes to realize that Addie is just as skilled at the con as him and just as cunning as and maybe even bolder than him.

Eventually they get involved with a semi-prostitute/showgirl Trixie Delight (Madeline Kahn) and her teenaged black maid, Imogene (P.J. Johnson). As Moses seems to be falling under her spell (the conman getting conned by the whiff of potential sex), Addie must team up with Imogene to break them up. It’s almost a love triangle, as Addie has to protect her man from the conniving tramp. The two must also maneuver away from a failed scam on a bootlegger and his corrupt sheriff brother (both roles played by John Hillerman). The continual scam and danger bring them closer together; the audience comes to realize that Moses is probably Addie’s actual father as Addie realizes it. Their growing bond is moving, while their continual conflicts are very funny.

In her first film role, the raspy-voiced Tatum is a natural. Of course she famously won the Best Supporting Actress Oscar, the youngest ever to do so at the time, though actually she’s much more than a supporting character, being in about every scene in the movie. Unlike most kid actors, she creates a fully rounded character with Addie. And also unlike most child performances that are created with a lot of quick edits, Paper Moon is shot in long takes of dialogue and action without cuts, a style of shooting that would be challenging to even seasoned actors. She would go on to have a couple more memorable films (The Bad News Bears, Little Darlings), but by adulthood her acting career would be fleeting, making more noise as a another lost child actor, now a tabloid pseudo celebrity.

Madeline Kahn’s overly feminine Trixie Delight is a sad woman still hanging on to her aging body as a survival chip. Her trying to connect with Addie, who is too wise, makes for some of the film’s best scenes. Paper Moon was only Kahn’s second film after her hilarious debut in What’s Up, Doc? (also directed by Bogdanovich and starring Ryan O’Neal). She would go on to appear in a number of films by Mel Brooks including most memorably as Lili Von Shtupp in Blazing Saddles. She would prove to be the dominant comic actress of the ‘70s (if only she had gotten to work with Woody Allen). In Paper Moon and her other films she manages to take bigger than life characters and infuse a realism and no matter how overly hammy the character, Kahn would bring a lot of vulnerability, turning sometimes cartoony characters into three-dimensional personalities. 

After the critical acclaim for The Last Picture Show and Paper Moon, the ever-confident Bogdanovich was flying high; his career would then go on an unprecedented nosedive with three mega-flops in a row (Daisy Miller, At Long Last Love, and Nickelodeon, all shockingly horrible). The days of the wunderkind were over, though he did have a few more decent flicks (Saint Jack, Mask) and has been fairly successful appearing as an actor (The Sopranos) and a respected film historian. (When he first came to Hollywood he was instantly buddy-buddy with Orson Welles and a number of old timers).

Paper Moon is a delight as a conman flick, but also nails the comedy and moves the heart as a relationship film. It’s also up there with The Grapes of Wrath when it comes to showing the despair of the Depression. So many of Moses and Addie’s victims are so open to being taken because they are so hopelessly wounded by the era they were stuck in. While Moses is looking for money and material wealth, Addie wants a father; the two find common ground by conning each other. The films echoes the period it depicts (you can feel a lot of everything from It Happened One Night to My Man Godfrey oozing off the screen). It’s no coincidence that Bogdanovich was buds with the masters of earlier generations, he learned from them well; like so many of their films Paper Moon stands the test of time, and is actually better than most the films it’s stealing from.

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Paper Moon was nominated for four Oscars including Best Supporting Actress (Madeline Kahn), Best Sound, and Best Adapted Screenplay (Alvin Sargent) and won for Best Supporting Actress (Tatum O’Neal).