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Director and screenwriter Andy Tennant made his way into film through acting and television directing. The Chicago native studied theatre under John Houseman at the University of Southern California and began acting in such films as Grease (1978), which allowed him to make use of his training as a dancer.

After getting his start in acting, Tennant became a television film scriptwriter and began directing TV films and series alike. He helmed multiple episodes of such shows as The Wonder Years, Parker Lewis Can't Lose, the popular sci-fi series Sliders, and the well-received drama Keep the Change (1992). He also gained a moderate dose of pop culture notoriety as the director of The Amy Fisher Story (1993).

Tennant made his feature film directorial debut in 1995 with It Takes Two, a children's film starring the Olsen twins. He then tried his hand at romantic comedy with Fools Rush In (1997), starring Salma Hayek and Matthew Perry. The following year, Tennant had his biggest cinematic success to date directing Drew Barrymore (whom he'd directed in The Amy Fisher Story five years earlier) in Ever After, a re-telling of the Cinderella fairy tale. Although the film received lukewarm reviews, it proved to be a commercial success, particularly among teenage girls. With commercial credibility to his name, Tennant subsequently directed Jodie Foster and Chow Yun-Fat in Anna and the King (1999), a sumptuous historical epic based upon the experiences of a British governess working in the court of the King of Siam.