He was supposed to appear in Sheryl Crow's video for "All I Wanna Do", but the director thought his dancing was too goofy so his part was removed.
Gregory went to University City High School In University City, Missouri, which is where he started first started learning the art of acting.
In 1998, he ran in the Big Sur Marathon (26.2 miles) in Carmel, CA, with a finishing time of 3:39:52 and coming in as the 395th runner.
He ran in the Chicago Marathon (26.2 miles) on October 22, 2000 with a finishing time of 03:04:11. (That's like 7 minutes a mile!) Maybe you saw him? His bib number was 30450.
During the week of October 16, 2000, Gregory returned to University City High to work with performing artists and students for the Annual Returning Artists Series.
His parents were social workers whose work in the community inspired him to start teaching.
He plays the trumpet, or at least did in high school.
Gregory danced in high school and was voted second best dancer in his senior year.
After high school, he went on to attend classes at Webster University, which he later left to pursue another path towards acting professionally.
He is among the Piven Theater Workshop's alumni, which also include Rosanna Arquette, Lara Flynn Boyle, Michael Byrne, Ann, Joan, John and Susie Cusack, Leelai Demoz, Amy Galper, Jaimie Gertz, Lecy Goranson, Thomas Greene V, Lauren Katz, Jay Kiecolt-Wahl, Zaks Lubin, Jeremy and Shira Piven, Aidan and Paul Quinn, Mary Kate Schellhardt, Eric Saiet, Eric Simonson, Tria Smith, Lili Taylor, Jessica Thebus, and Kate Walsh.
His first starring role was in "Say Anything..." starring John Cusack.
Gregory has been working on a screenplay about the marathon race that was the highlight of St. Louis' 1904 World Fair.
After finishing shooting "Black Hawk Down," Gregory got married his wife, Meghan.
