- His first on-screen kiss was with Kirsten Dunst in Small Soldiers (1998).
- His first gig was at the age of 14 months when he was in a Tide commercial.
- He began acting seriously at the age of 6.
- His hobbies are acting, rock climbing, soccer, rollerblading, and photography.
- His father, Maurice Smith, is English-born (from London), and his mother, Terrea (Oster), is American-born (from California). Gregory has English, Ashkenazi Jewish, and small amounts of Dutch, German, Swedish, and Norwegian, ancestry.
- Dual citizen of the U.S. and Canada.
- Has two younger brothers, Andrew and Douglas, and a younger sister, Samantha.
- During the making of American Outlaws (2001) Smith, the youngest of the cast, got the nickname 'Secret Weapon' from the wranglers, for his rare talent to handle guns.
- Has two other siblings named Andrew and Samantha.
- Is allergic to cats.
- His parents separated when he was 12 years old
- Father of son, Harry Edward and daughter, Primrose Elizabeth.
- He broke his collar bone while skiing.
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