In Sofia Coppola‘s latest film, The Beguiled, due out in theaters this Friday, Colin Farrell plays John McBurney, a wounded soldier brought in by a small, Southern all-girls school in order to convalesce. His male presence quickly stirs the household, as several of the ladies at hand begin to play for his affection—and he is more than willing to flirt back. It’s a role that Farrell has seemingly been preparing for all of this life—or at least since 1999, when he made his Hollywood debut in The War Zone. Since then, Farrell quickly made a name for himself as one of the world’s most famous bachelors. At the height of his bad boy-dom, the actor had flings with Lindsay Lohan and Britney Spears, as well as a rumored fling with Alexander co-star Angelina Jolie. Recently, Farrell also revealed he had a romantic relationship with Elizabeth Taylor at the end of her life, before being spotted out with Rihanna, proving that he is not one to have a “type.” Here, a look back at his most public relationships.