She began her career with smaller roles, including appearances in Viper and a brief role in Adam Sandler’s Happy Gilmore. She later spoke fondly of her time on set, describing Sandler as kind and supportive. Fleming’s breakthrough in the horror genre came in 2005 when she appeared in Masters of Horror, gaining attention for her bold and memorable performance. She went on to appear in films like The Tooth Fairy and Bloodsuckers.
Many fans remember her as Karen Singer on Supernatural, the warm-hearted wife of Bobby Singer. She also had a recurring role on iZombie and appeared in several TV movies, including The Unauthorized Full House Story. In recent years, Fleming remained active in both television and stage productions. Jim Beaver paid tribute, calling her a “powerhouse of vitality” with an unforgettable personality. She is survived by her daughter, Madalyn Rose.