In 2000, a time when Ryan's "America's Sweetheart" reputation was well-established, Ryan was accused of cheating on her then husband, which did much to degrade her public image.
She attempted to rebrand with several projects in the 2000s, notably the erotic thriller "In the Cut," which featured a nude scene and an overall sexier atmosphere.
None of these later projects was a major success, and 2008's "The Women," and 2009's "Serious Moonlight" were critical disasters. After 2009, she retreated from the spotlight.
In 2015, Ryan returned with her directorial debut, "Ithaca," which was another critical disappointment. She took another long break before directing 2023’s "What Happens Later."
In 2023, Ryan told People, "I took a giant break because I felt like there's just so many other parts of my experience as a human being I wanted to develop."
In addition, at the Sarajevo Film Festival, she also spoke about women struggling to find roles after a certain age, stating this prompted her to pursue producing and directing.