[2] 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.
[4] On the big screen, Henry appeared in the Brat Pack film Sixteen Candles (1984), as Mike, one of main character Samantha's siblings.
In this role, critic Janet Maslin called him a "large and amusingly sullen teenager".
[5] 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.
[4] 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.