After Carl 's best man and friend Randolph Dupree ( usually just called `` Dupree '' ) ( Owen Wilson ) , loses his job and apartment , the couple allow him to move in but Dupree inevitably overstays his welcome . After Carl 's best man and friend Randolph Dupree ( Owen Wilson ) , loses his job and apartment , the couple allow him to move in but Dupree inevitably overstays his welcome .