The Talented Mr. Ripley (1999)

Ambitious bathroom attendant Tom Ripley (Matt Damon) attempts to pull his life out of the toilet by pretending to be a wealthy young jet-setter in the psychological thriller The Talented Mr. Ripley (1999). Based on Patricia Highsmith’s same-named novel, Anthony Minghella’s R rated flick was a critical hit — nabbing five Academy Award nominations as well as a statuette in Mr. Man’s pants! If that’s not successful enough, the movie was both a box office and spank bank smash! The 1950s-set drama follows Tom as he passes himself off as a Princeton grad to some wealthy dad named Herbert Greenleaf (James Rebhorn). One con leads to another and the next thing you know Tom is mingling with Herbert’s son Dickey (Jude Law) in Italy. There, Tom tries to convince Dick to split with his girlfriend Marge (Gwyneth Paltrow) and return to the States. But his scheme loses its sheen when Dickey and his pal Freddie Miles (Philip Seymour Hoffman) discover that talented Tom is not who he seems. Others who are growing suspicious include Peter Smith-Kingsley (Jack Davenport), Meredith Logue (Cate Blanchett), and Inspector Roverini (Sergio Rubini). Although Leonardo DiCaprio was first offered Damon’s role, Matt impressed flesh fans with his bare back and ass flash. Of course, he pales compared to Jude, who touts his charismatic assets on screen. In addition to exposing his hairy chest, the skintastic stud shows off his firm bum and big cock when he gets out of the bath. No wonder, his character is called Dickie!