Five Great Flicks Featuring Con Artists

April Fool’s Day is upon us where we all get free reign to play pranks on one another and lie with impunity. In the spirit of this holiday, here are five note-worthy films celebrating hoaxsters, tricksters, and plain old flim-flam men. Enjoy! (But watch your wallet.)

The Music Man (1962) Based on the Broadway musical of the same name, Robert Preston’s performance of slick tongued salesman Harold Hill and how he transforms and is transformed in turn by River City, Iowa is one of the most iconic of all time. Also starring Buddy Hackett, Shirley Jones, and Paul Ford it was one of the highest grossing films of the year. It won the Academy Award for Best Musical Score and was nominated for five more including Best Picture. It later holds up as one of the best and most beloved movie musicals of all time and indeed ‘Harold Hill’ has now become cultural shorthand for swindlers everywhere!

The Sting (1973) Directed by the legendary George Roy Hill (Butch Cassidy and the Sundance Kid) and starring Paul Newman and Robert Redford as two professional grifter’s in the Depression era, who pull on a complicated confidence scam on a mob boss played by Robert Shaw. A box office smash, The Sting was nominated for 10 Oscar Awards and won seven including Best Picture, Best Director, and Best Original Screenplay.

Six Degrees of Separation (1993)  Directed by Frank Schepesi and adapted from the Pulitzer Prize nominated John Guare play of the same name and based on the true story of David Hampton. Fifth Avenue Socialite Ouisa Kittredge (Stockard Channing) and her husband Flan (Donald Sutherland) get taken in by slick young hustler Paul (Will Smith in his first major film debut) who convinces them that he’s the son of Sidney Poitier. Stockard Channing’s performance was nominated for both a Golden Globe and an Academy Award.

Catch Me If You Can (2002) Steven Spielburg directed this biographical crime film based on the life of Frank Abagnale who successfully impersonated a pilot, a doctor, a lawyer and made off with huge sums of cash-while he was still a teenager. Leonardo DiCaprio gives an astonishing performance as Frank, Christopher Walken plays his father Frank Sr., and Tom Hanks is Carl Hanratty, the FBI agent assigned to take him down. It was a financial and critical success with a 96% fresh rating at Rotten Tomatoes and Christopher Walken was nominated for an Academy Award.

The Hoax (2006) Directed by Lasse Halstrom (The Cider House Rules, What’s Eating Gilbert Grape?) and starring Richard Gere as Clifford Irving. It tells the story of Irving’s elaborate hoax of writing and publishing the autobiography of Howard Hughes – without ever even speaking to Howard Hughes himself. Anchored by Gere’s performance the movie also sports an all star cast including Al Molina, Hope Davis, Marcia Gay Harden, and Stanley Tucci. Which helps explain why it made the Top 10 Films lists for both the Los Angeles Times and Newsweek.

About Winnefred Ann Frolik (155 Articles)
Winnefred Ann Frolik (Winnie for short) was born and raised in Pittsburgh, Pennsylvania. She completed the International Baccleareate program at Schenley High School and then attended the University of Pittsburgh where she completed a double major in English Literature and Creative Writing. After graduation she spent a number of years working in the non-profit sector and it was during that phase in her life she moved to D.C.  Winnie co-wrote a book on women in the U.S. Senate with Billy Herzig.  She enrolled in a baking program in culinary school and worked in food services for a while. She currently works in personal services while writing for Woman Around Town and doing other freelance writing projects including feeble personal attempts at fiction. Her brother is a reporter in Dayton, Ohio so clearly there are strong writing genes in the family.  She lives in Pittsburgh, PA, with two demanding cats.