No matter what happens atSunday night's Oscars, Leonardo DiCaprio and Kate Winslet's 20-year friendship will keep being strong. Oscar winner, Winslet remains by the side of Oscar nominee DiCaprio. Ever since these two shot the 1996 box office hit, Titanic, they've been supporting each other. FOr two decaes now, this dynamic duo has had eachothers backs.. More than Rose had Jack's, for sure.