- Graduated from Columbia University with a degree in film (2002)
- He is an accomplished guitarist.
- Made his first television appearance as an infant in a Q-tip commercial.
- Homecoming king at his high school.
- Jesse's paternal grandfather, Curtiss Baldwin Watrouse, was from a family that has lived in New England since the 1600s (they were of English descent, and the surname was originally spelled "Waterhouse"). His paternal grandmother, Florence Louise Bradford (the origin of his stage name), was from Hackney, London, England. Jesse's mother is of Polish ancestry.
- Was cast member in Presunto innocente (1990) as a child with two other future West Wing - Tutti gli uomini del Presidente (1999) cast members: John Spencer and Bradley Whitford.
- Shares his name with two fictional female characters. One played by Lara Flynn Boyle in the 1987 mini-series Amerika (1987), and the other one played by Olivia Hussey in the horror film Black Christmas (Un Natale rosso sangue) (1974).
- He took French in high school but Spanish in college.
- Born on exactly the same date as Monica Keena (of "Freddy VS Jason" and "Man of the House" fame).
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