Gregory began his career at the age of 14 and appeared in a Tide television commercial and in-store catalogs. He made his movie debut in a 1994 American family drama film Andre, which was directed by George Miller. The stars of this movie are Keith Carradine, Tina Majorino, Keith Szarabajka and Chelsea Field.
In 2002, Gregory appeared in an American epic historical fiction war film The Patriot. The movie was directed by Roland Emmerich. The cast members of this movie are Mel Gibson, Heath Ledger, Joely Richardson, and Chris Cooper. The movie became a huge hit and grossed $215.3 million at the box office against the budget of $110 million.
In 2013, Gregory featured in an American psychological thriller film Dream House which was directed by Jim Sheridan. The stars of this movie are Daniel Craig, Rachel Weisz, Naomi Watts, and Marton Csokas. The total budget for this movie was $50 million and grossed $38.5 million at the box office.
Similarly, Gregory has appeared in numerous movies including Big Bully, The Climb, Zenon: Girl of the 21st Century, American Outlaws, Nearing Grace, Boot Camp, Edison and Leo, and Conception. Likewise, he also featured in some hit television series The Commish, The Hat Squad, Mega Man, Touched by an Angel, Rookie Blue, Working the Engels, and Designated Survivor.
Gregory holds dual nationality, Canada, and American and comes from English and Ashkenazi ethnic background. Talking about his love life, he dated his girlfriend Elizabeth Gooen. After he broke up with Elizabeth, he began dating Melissa Schuman in 2003. However, the couple was unable to continue their relationship for a long time and separated from each other in the same year.
Soon he got broke up with Melissa and romantically involved in a relationship with Ashlee Simpson. The couple lived in a relationship for a year and broke up in 2004. Currently, he is unmarried but we hope that he will soon get married to his wife in front of media. He does not have any children.
Having played roles in numerous movies and television series, Gregory has banked $90,000,000. His net worth is an outcome of his career as an actor and endorsements. He also gets paid for ads, sponsorship, featuring, endorsement etc. His early incomes can be estimated at $10,588,235 and he earns $2,352,941 only through endorsement or sponsorships.