- He founded a theater company called Malaparte with Ethan Hawke, Robert Sean Leonard, and Steve Zahn.
- Does all his own musical work whenever he plays a musician in a movie.
- Is good friends with actor Ethan Hawke, who also lists Whaley in the acknowledgments of one of his novels, Ash Wednesday.
- As of 2022, he has appeared in four films that were nominated for the Best Picture Oscar: L'uomo dei sogni (1989), Nato il quattro luglio (1989), JFK - Un caso ancora aperto (1991) and Pulp Fiction (1994).
- Good friends with actor Val Kilmer.
- Graduate of State University of New York at Albany.
- Made his acting debut on the New York stage in Tigers Wild.
- Listed as one of twelve "Promising New Actors of 1991" in John Willis's Screen World, Vol. 43.
- A staunch supporter of indie films, he hosted the MetroChannel cable TV's Metro-Angelika Film Festival (2001).
- Played Lee Harvey Oswald in Mio marito è innocente (1993) and an Oswald impostor in JFK - Un caso ancora aperto (1991).
- He is of Irish and Italian/Sicilian descent.
- Wife Heather Whaley, graduate of Colby College, is a playwright and actress, author of "Social Notes: An Evening with Dorothy Parker".
- Plays bit parts in big movies and successful star vehicles (Pulp Fiction (1994), JFK - Un caso ancora aperto (1991), Nome in codice: Broken Arrow (1996), Il boss e la matricola (1990), Nato il quattro luglio (1989) and Red Dragon (2002)), and leads in mostly small and unsuccessful movies (Tutto può accadere (1991), Una notte, un cane, un sogno (1990), and The Jimmy Show (2001)).
- He has appeared in two films that have been selected for the National Film Registry by the Library of Congress as being "culturally, historically or aesthetically" significant: L'uomo dei sogni (1989) and Pulp Fiction (1994).
- Gained 30 pounds for role in L'ultima occasione (1995).
- Auditioned for the role of Link Larkin in Grasso è bello (1988). The role was eventually played by Michael St. Gerard.
- Son of Josephine and Robert W. Whaley Sr.
- His brother is musician/composer/actor Robert Whaley and also has two sisters.
- In Piccoli mostri (1989) plays a character named Boy, and in Il prezzo di Hollywood (1994) plays a character named Guy.
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