 One of the most critically and commercially successful films of Hoffman 's career was The Talented Mr. Ripley ( 1999 ) , which he considered " as edgy as you can get for a Hollywood movie " . He played a " preppy bully " who taunts Matt Damon 's Ripley in the thriller , a character which Jeff Simon of The Buffalo News called " the truest upper class twit in all of American movies " . Hoffman 's performance caught the attention of Meryl Streep – another of his cinematic idols – with his performance : " I sat up straight in my seat and said , ' Who is that ? ' I thought to myself : My God , this actor is fearless . He 's done what we all strive for – he 's given this awful character the respect he deserves , and he 's made him fascinating . " In recognition of his work in Magnolia and The Talented Mr. Ripley , Hoffman was named the year 's Best Supporting Actor by the National Board of Review . 
