I was sitting watching the new episode of Mad Men and I wondered where the notorious womanizer Roger Sterling would fall on the Big Five personality inventory:
Roger is an extremely extraverted person, always seen flirting with women and schmoozing clients. As if he couldn't get any more extraverted, he becomes even more so after a few drinks, which tends to be the majority of the time.
Roger is without a doubt an entertainer because in addition to having high extraversion, he has very low conscientiousness. He often times rushes into things, doesn't think through all the details and often refuses to accept responsibility.
Roger is moderate on Openness to Experience. This is apparent through his work habits which consist of show up to work, drink and smoke heavily, hit on women, sleep, and repeat. Roger continues his habits even after being told to quit by his doctor in the wake of two almost fatal heart attacks. However, Roger does go through a divorce and remarriage to a significantly younger spouse, although a new experience probably isn't the primary cause.
Agreeableness is a category Roger is severely lacking in. He tends to be easily angered especially when someone takes shots at his ego and sees things as "my way or the highway" (agree with me or I will fire you). Roger's tends to be emotionally cold, but occasionally has neurotic periods where his mood swings rapidly especially with his quick and eccentric temper.