11. Kelly Cutrone
And speaking of Cutrone, their scary boss ended up also playing a large role in The City, employing Port and mentoring her on her clothing line. She went on to star in her own series for Bravo, Kell on Earth, published a memoir and served as a judge on America's Next Top Model.
Cutrone was recently spotted at New York Fashion Week with The Hills alum Audrina Patridge and continues her reality TV streak with an all-new series for CW, titled The Kelly Cutrone Project, that premiered earlier this month. The first episode guest starred Joe Zee, editor-in-chief of Yahoo Style, who also appeared on The City.