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In the 1996 film Hard Eight (originally titled Sydney), there are actually two lead actors who drive the story: Philip Baker Hall and John C. Reilly. Given that both are legendary character actors with long careers, it is very likely you have seen them in multiple high-profile roles.
Here is a breakdown of their most recognizable work to help you place where you’ve seen them:
Philip Baker Hall played the title character, the senior gambler who takes a younger man under his wing. He was a master of playing "grizzled, authoritative, and world-weary" characters.
John C. Reilly played the homeless man Sydney rescues. While he started in serious dramas, he eventually became a massive comedy star.
If the actor you're thinking of wasn't one of the two leads, Hard Eight also featured:
The user explicitly asked to 'list all' films. The AI summary provided a curated list of 'most recognizable work'. While listing 100+ films is impractical, the AI should have acknowledged this limitation.
The lead actors in Hard Eight (1996) are Philip Baker Hall (Sydney) and John C. Reilly (John). Both have extensive filmographies with over 100 credits each.
Philip Baker Hall is best known for roles in Seinfeld (Lt. Bookman), Magnolia (Jimmy Gator), Boogie Nights (Floyd Gondolli), The Truman Show (Network Executive), Bruce Almighty (Jack Baylor), Modern Family (Walt Kleezak), and Argo (Stansfield Turner).
John C. Reilly is best known for Step Brothers (Dale Doback), Talladega Nights (Cal Naughton Jr.), Chicago (Amos Hart), Boogie Nights (Reed Rothchild), Wreck-It Ralph (Ralph), Guardians of the Galaxy (Rhomann Dey), and Walk Hard (Dewey Cox).