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Constantine may best be remembered as a Keanu Reeves vehicle, but the cast of the 2005 film is also distinctive because it included two future Oscar winners, as well as a young actor who would become a big star. Based on the Hellblazer comics, it featured Englishwomen Rachel Weisz and Tilda Swinton. Just one year after her turn as the twins Angela and Isabel Dodson in Constantine, Weisz -- her Mummy days clearly behind her -- won a best supporting actress Academy Award for The Constant Gardener (which was released the same year as Constantine). And three years after her interpretation of the angel Gabriel, Tilda Swinton garnered a best supporting actress Oscar as well for Michael Clayton (2007). Shia LaBeouf may not have taken home any statues in the interim since playing Constantine's apprentice Chas Kramer, but he's become a breakout star, carrying films like Transformers (and its forthcoming sequel), Eagle Eye. Not to mention, he is talked about as the possible heir to the Indiana Jones franchise.
Other movies with future Academy Award winner pairings?
Miss Firecracker (1989): True, Holly Hunter was already a star because of Broadcast News (1987), but she wouldn't have that coveted Oscar until her turn in The Piano (1993). Tim Robbins had yet to hit it big when he made this movie and would wait more than a decade until he got his award, as best supporting actor, for Mystic River (2003).
The Rocketeer (1991): This movie -- of which the costumes and scenery were considered "considerably wittier" than the people -- starred Jennifer Connelly and featured Alan Arkin, before the former became best supporting actress for A Beautiful Mind (2001) and the latter was the best supporting actor of 2006 for Little Miss Sunshine.
Christopher Columbus: The Discovery (1992): This fairly unmemorable flick boasted Catherine Zeta-Jones (without the hyphen back then) and Benicio Del Toro in its cast. Zeta-Jones would go on to marry well (Michael Douglas) and win best supporting actress for Chicago (2002). Meanwhile, Del Toro made it to the Oscar stage in 2001, as best supporting actor for Traffic (2000)... which also starred Zeta-Jones and Douglas.
Species (1995): This scifi thriller only had one future Oscar winner: Forest Whitaker, who would win best actor for The Last King of Scotland (2006). But also in the cast was a teenaged Michelle Williams, three years before Dawson's Creek and ten years before her nomination for Brokeback Mountain (2005).