Mary O'Connor's Life Inside the Playboy Mansion

For four decades, Hugh Hefner's longtime secretary was a constant source of companionship for the Playboy founder and his bunnies

ONE OF THE GIRLS

Her appearances on The Girls Next Door often saw O'Connor providing advice and guidance to the show's stars, Bridget Marquardt and Holly Madison, whom she joined at the Derby alongside Hef, his brother Keith and artist LeRoy Neiman. "She was so giving and helpful to so many and has left a legacy of wonderful friendships, memories and so much more," Madison told PEOPLE.