 In June 1982 , Brown , then a 22 @-@ year @-@ old law student at Boston College , won Cosmopolitan magazine 's " America 's Sexiest Man " contest . After two weeks on a crash diet of " three cans of tuna a day " and intensive workouts he was featured in the magazine 's centerfold , posing nude but strategically positioned so that according to Brown , " You don 't see anything " . In the accompanying interview , he referred to himself as " a bit of a patriot " and stated that he had political ambitions . The Cosmopolitan appearance and its $ 1 @,@ 000 fee helped pay for law school , and began for Brown a " long , lucrative " part @-@ time catalog and print modeling career in New York and Boston during the 1980s . Brown took a leave of absence from Boston College and further pursued his modeling career in New York where he was represented by Wilhelmina Models while taking classes at the Benjamin N. Cardozo School of Law . He returned to Boston , after nearly two years , to continue his studies at Boston College and continued to work as a model represented by Boston agent , Maggie Trichon of Maggie Inc . 
