A cikin Passage: About Schmidt (2002), Nicholson ya nuna wani mai ritaya na Omaha, Nebraska, wanda ya yi tambaya game da rayuwarsa bayan mutuwar matarsa. Ayyukansa na kwanciyar hankali ya ba shi lambar yabo ta Academy Award don Mafi kyawun Actor. A cikin Anger Management (2003), ya taka leda a matsayin mai ilimin likitanci wanda aka ba shi izini don taimakawa wani mutum mai zaman lafiya (Adam Sandler). A 2003, Nicholson ya kuma taka rawa a cikin Wani abu ya ba da Gotta, a matsayin mai tsufa mai wasan kwaikwayo wanda ya ƙaunaci mahaifiyar (Diane Keaton) na saurayi budurwa. A ƙarshen 2006, Nicholson ya nuna komawarsa zuwa duhu a matsayin Frank Cost, wani dan wasan Irish na Boston Mobello, wanda ya dogara da Whitey Bulger wanda har yanzu yana gudana a wannan lokacin, yana jagorantar Matt Damon da Leonardo DiCaprio a cikin fim din Martin Scorsese na Oscar wanda ya lashe kyautar Oscar, wanda ya sake yin aikin Andrew Laufer a matsayin mai ba da shawara. A cikin Tambaya game da Abin da Schmidt ya yi, Nicholson ya fito ne tare da lambar yabo ta duniya da dama, ciki har da lambar yabo ta Golden
Shekarar 2002