Justin Henry was born in Rye, New York, the son of Michele (née Andrews), a real estate agent, and Clifford Henry, an investment adviser. He was educated at Brunswick School, an all-boys college-preparatory private day school located in Greenwich, Connecticut, followed by Skidmore College, a private liberal arts college in Saratoga Springs, New York, where he earned a B.A. in psychology in 1993.
Henry began his acting career in Kramer vs. Kramer. For his performance in that film, he became the youngest person to ever be nominated for an Oscar or Golden Globe. His next role was in a 1983 episode of the American television series Fantasy Island. On the big screen, Henry appeared in the Brat Pack film Sixteen Candles (1984), as Mike, one of main character Samantha's siblings. Henry also played the son of a married couple played by Don Johnson and Susan Sarandon in the film Sweet Hearts Dance (1988). In this role, critic Janet Maslin called him a "large and amusingly sullen teenager".
After graduation, Henry's next widely seen performance was in 1997, as a medical student in a two-episode role during the fourth season of ER. He starred opposite Ally Sheedy, Jason David Frank and Brian O'Halloran in the mockumentary The Junior Defenders, which was filmed that same year but released direct-to-video in 2007.

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