Here's some of Cruise's filmography in the late '80s and '90s: "Top Gun" and "The Color of Money" (1986), "Cocktail" and "Rain Man" (1988), "Born on the Fourth of July" (1989), "Days of Thunder" (1990), "A Few Good Men" (1992), "Interview with the Vampire" (1994), "Mission: Impossible" and "Jerry Maguire" (1996), and "Eyes Wide Shut" and "Magnolia" (1999). Maybe you've heard of him now, but at the time, Cruise was a relatively green 21-year-old actor who had only been in two movies: "Endless Love" and "Taps." He had small roles in all three films.īut, five months after "The Outsiders," a film called "Risky Business" was released, catapulting Cruise to the A-list. Ron Galella/Ron Galella Collection via Getty Images They were divorced by 1994.Įstevez, 59, is frequently working behind the camera, though he reprised his role as Gordon Bombay in "The Mighty Ducks: Game Changers" in 2021. He has two kids with former model Carey Salley - their relationship overlapped with Estevez's engagement to Moore. This Is Now," and "Young Guns." He also made his directorial debut with 1986's "Wisdom," co-starring his then-girlfriend Demi Moore.Įstevez had his biggest adult role in 1992's "The Mighty Ducks," which led to two more sequels in the '90s, "D2: The Mighty Ducks" in 1994 and "D3: The Mighty Ducks" in 1996 as prickly coach Gordon Bombay. Ron Galella, Ltd./Ron Galella Collection via Getty ImagesĮstevez was 21 at the time of "The Outsiders." Along with Lowe, Estevez - whose father is Martin Sheen and brother is Charlie Sheen - became a major member of the Brat Pack, with roles in "Tex" (alongside Matt Dillon), "The Breakfast Club," "St. Ralph Macchio played the sweet Johnny Cade, who cautions Ponyboy to "stay gold."Įmilio Estevez in 1984. He's set to appear in "American Dreamer," based on a segment from "This American Life," alongside Peter Dinklage, Shirley MacLaine, Danny Glover, and Danny Pudi. He's also moved into TV, appearing on "Modern Family," and the first season of "Wayward Pines," which earned him a Saturn Award nomination. He then appeared in comedies such as "Herbie: Fully Loaded," "You, Me and Dupree," "Girl Most Likely," "The Art of the Steal," and "Old Dogs," in addition to dramatic films like "Loverboy," "Sunlight Jr.," and most recently the Tom Hardy-led "Capone." Dillon starred in the 2018 Lars von Trier film "The House That Jack Built." The film itself won the Oscar for best picture. Two years later, he starred in "Crash," which garnered him a Golden Globe nomination, an Oscar nomination, and a SAG nomination, among others. Carlos Alvarez/Getty Imagesĭillon made his directorial debut with 2002 film "City of Ghosts," to mixed reviews. He continued to establish Hollywood dominance in the '90s with roles in "Singles," "There's Something About Mary," and "Wild Things."ĭuring this time, he also dated multiple A-listers, like Cameron Diaz, Heather Graham, and Brooke Shields.ĭillon, 57, was nominated for an Oscar for his role in 2004's "Crash." Hinton adaptation "Rumble Fish," "The Flamingo Kid," "Kansas," and "Drugstore Cowboy," which earned him an Independent Spirit Award. Hinton adaptation, "Tex," the year before "The Outsiders," along with films "Over the Edge," "My Bodyguard," and "Little Darlings." He solidified his teen-idol status with "Outsiders," another S. He meets a heartbreaking end that we won't spoil, but it's possible the trend of "broken" teenage boys may have started with Dally.ĭillon had already appeared in another S. Ron Galella/Ron Galella Collection via Getty Imagesĭillon was 19 when "The Outsiders" was released, fittingly, as Dally was an older character in the novel and the film.