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jfk obrien ache. Leo’s career in the entertainment industry Lenny Bruce once said, "You can't be a great comedian and have no talent." Leo Kross was able to accomplish this by being versatile in his act. He could play all sorts of roles- from the goofy sidekick to the hard-hitting villain- and still maintain his audience's attention. Kross began his career as a character actor, playing supporting parts in films such as The Three Musketeers and Roman Holiday. In 1961, he starred in the feature film Thank You for Smoking, which became a critical and box office success. That same year, Kross won an Academy Award for Best Supporting Actor for his role in Smokey and the Bandit. After Thank You for Smoking, Kross returned to television with shows such as The Honeymooners and The Monkees.