Following in his father's stead, Michael Cuesta began his career as a photographer before segueing to directing commercials. Eventually, though, he moved into writing and directing feature films and he earned nearly unanimous praise for the well-crafted, controversial "L.I.E." (2001). Raised on Long Island in the tony community of Dix Hills, Cuesta spent two high school summer vacations working as a newspaper intern and photojournalist in Puerto Rico. After attending NYC's School of Visual Arts, he marked time as a photographer's assistant before eventually opening his own shop (as his father had). The Michael Cuesta Studio shot advertising campaigns for such clients as Coca-Cola and Dupont. By 1992, though, Cuesta has made the move to film, shooting tabletop work for the now-defunct London-based firm Jennie & Co. Within six months, he had switched employers and became ensconced at A+R New York and went on to create hundreds of commercials.

In 1995, Cuesta began to write a semi-autobiographical drama about growing up on Long Island. By his own admission, he had run "with a crowd and we caused a little trouble, but I was always much more into books and movies and I always carried a camera." Still, the seed for what would become his first full-length feature was sown. Over the next five years, Cuesta would refine the screenplay with help from his brother Gerald and college pal Steve Ryder. Eventually what emerged was a contemporary snapshot of disaffected suburban teens. The film's protagonist is a young boy on the cusp of manhood struggling with his burgeoning sexual feelings, his attraction to his charismatic best friend and his odd but chaste relationship with an ex-Marine who happens to be a pedophile. Shot almost like a documentary, "L.I.E." (which stands for Long Island Expressway as well as the obvious) garnered strong notices at Sundance and was picked up for distribution by Lot 47 Films.