CBS cameraman Harry Hinkle (Lemmon) is injured when Cleveland Browns player Luther "Boom Boom" Jackson (Ron Rich) collides with him during a game. Harry's injuries are slight, but his brother-in-law, fast-talking attorney "Whiplash Willie" Gingrich (Matthau), sees the chance for a big insurance payment if Harry exaggerates them. What follows next is a comedy of deception mixed with the drama of remorse, as Harry sees the affects of the con on the guilt-ridden player. Meanwhile, the insurance company—convinced that something devious is afoot—hires private detective Chester Purkey (Cliff Osmond) to keep Harry under surveillance.
Nominated for four Academy Awards, with Matthau winning Best Supporting Actor for his performance.
- Ambulance Chaser: Whiplash Willie.
- Batman Gambit: The P.I. Purkey successfully employs one of these against Hinkle.
- Be Careful What You Wish For: Harry has been pining for his ex-wife since she left him. Once she comes back into his life after the accident he realizes she's as scheming as Willie.
- Beware the Nice Ones: Harry, when he calls out his ex-wife for her cold Gold Digger attitude.
- Butt-Monkey: Poor Harry Hinkle. His wife left him, and his brother-in-law is constantly trying to use his accident as a means to make money.
- The Cameo: Sportscaster Keith Jackson (who in real life worked for ABC rather than CBS) is seen calling the Browns game in the opening scene.
- Control Freak: Willie, keeps trying to control Harry's life in order for his scheme to work, he nags Harry into going along with it.
- Deliberately Monochrome: This was the last of Wilder's films shot in black and white. In part this was done to mirror TV production values, as most broadcasts at the time still aired in B&W (although this changed soon afterwards).
- Easily Forgiven: Jackson seems to take it well that Harry and Willie were lying to him about Harry's condition.
- Flirtatious Smack on the Ass: Willie gives one to Harry's ex-wife.
- Frivolous Lawsuit / Insurance Fraud
- Gold Digger: Harry Hinkle's ex-wife reenters the picture when she thinks he's going to get rich off the lawsuit.
- Hilarity Sues
- Market-Based Title: Released as Meet Whiplash Willie in the UK.
- Nice Guy: Luther "Boom Boom" Jackson
- Obfuscating Disability
- Pretend Prejudice: Part of the aforementioned Batman Gambit. Deconstructed in that, as Willie demonstrates, it could still be used against the perpetrator.
- Sensitive Guy and Manly Man: Harry and Willie, respectively.
- Shout-Out: Willie likes to hum the prelude of The Barber of Seville by Gioachino Rossini. Indeed, he is as cunning as Figaro.
- Spectator Casualty: An incident of this starts the plot when Hinkle is accidentally knocked down by a football player.