Gilpin began her acting career with guest starring roles in numerous television series, including Law & Order: Criminal Intent, Fringe, Medium, Law & Order: Special Victims Unit, and Elementary. She received further recognition for her starring role as Dr. Carrie Roman in the comedy-drama series Nurse Jackie, appearing from 2013 to the series' conclusion in 2015.
Gilpin appears in supporting roles in such films as Ghost Town (2008), Take Care (2014), True Story (2015), and Future '38 (2017).
Gilpin has also appeared off-Broadway in productions such as Heartless, I'm Gonna Pray for You So Hard, and We Live Here.
Gilpin's breakthrough came with her starring role as Debbie "Liberty Belle" Eagan in the Netflix comedy series GLOW (2017–present), which was inspired by the 1980s female professional wrestling league of the same name. She received significant critical acclaim and numerous award nominations for her performance, including two Critics' Choice Television Award for Best Supporting Actress in a Comedy Series and two Primetime Emmy Awards for Outstanding Supporting Actress in a Comedy Series.
In 2019, Gilpin appeared in the fantasy romantic comedy film Isn't It Romantic, the comedy-drama film A Dog's Journey, the action comedy film Stuber, and the action horror film The Hunt.
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