In the 1990s, Whitfield played leading roles in a number of made-for-television movies and had several starring roles in theatrical films, including A Thin Line Between Love and Hate (1996), Gone Fishin' (1997), Eve's Bayou (1997), Stepmom (1998), Head of State (2003), Madea's Family Reunion (2006), and The Women (2008). Whitfield also starred in a number of movies in the 2000s and 2010s. From 2016 to 2020, she starred as Lady Mae Greenleaf in the Oprah Winfrey Network dramatic series Greenleaf, for which she won critical acclaim and garnered two NAACP Image Awards and a Gracie Award