- Casting Gag: Along with several other Band of Brothers cast members, he voiced soldiers in Call of Duty.
- The Chew Toy: There are plenty of stories of the military advisors setting him up to get pranked on the set of Band of Brothers.
- Contractual Purity: Averted. He began doing family friendly stuff, with Hook and guest spots on sitcoms - but Hero and The Basketball Diaries were edgy enough to avoid this trope.
- The Danza: As James Bronson in Applebox. Also as Jimmy Donuts in Glenn Martin DDS.
- Dawson Casting: He was twenty when he played a drug addict teenager in The Basketball Diaries and played Lazz in USA High at twenty four.
- Dyeing for Your Art: Endured a ten day boot camp for Band of Brothers where he had to remain in character almost all the time. Also shaved his head for a role in The Box.
- Memetic Badass: As far as his BOB cast members go. During the ten year anniversary interviews, half of them told a story about James Madio starting a bar fight in Soho. Proving how this trope can go, James's version says he went down to prevent a fight.
- Playing Against Type: In the show Queens Supreme as a law clerk. Also in The Week where he plays the protagonist's concerned best friend.
- Playing with Character Type: In the sci-fi film The Last Push where he's the Plucky Comic Relief - who's killed off within the first ten minutes and his friend starts to hallucinate about him.
- Production Posse: The film The Week alongside Rick Gomez, Frank John Hughes and Richard Speight Jr. All of them also appear in James's short Applebox.
- Real-Life Relative: His father worked as an extra in Hook playing one of the pirates.
- Typecasting: He'll usually be cast as characters that have Brooklyn Rage or that serve as the Plucky Comic Relief.
- What Could Have Been:
- He auditioned for BOB reading for the part of Guarnere, which eventually went to Frank John Hughes.
- The scene where he delivered a "Reason You Suck" Speech to O'Keefe in Episode 9. According to James, he wanted to physically attack O'Keefe and pull a gun on him. The director suggested he do the scene reading a book instead. James says that the change was absolutely for the better.
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