Bad Boy (2002)

A lifelong womanizer (Doug 'Dawg' Munford, played by 'Denis Leary') learns upon his grandmother's death that he stands to inherit her full fortune - that he was unaware she had accrued - pending his fulfillment of conditions set forth in her last will & testament, according to her strikingly beautiful, savvy attorney ('Anna Lockheart', played by Elizabeth Hurley), who would be charged with accompanying him on his journey in order to ensure he properly & honestly accomplishes the "mission", which is to locate and elicit forgiveness from 1 dozen of his former conquests, if he chooses to accept it. Bickering, adventure, road trip, and a few surprises ensue featuring lawyer & heir as they encounter an eclectic array of interesting characters from his past, eventually leading to an opportunity for him to reflect on his lifestyle. Did Grandma have an ulterior motive?