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Lohan became known as a triple threat after signing with Casablanca Records and releasing two studio albums, the platinum-certified Speak (2004) and gold-certified A Little More Personal (Raw) (2005). She also starred in the comedies Herbie: Fully Loaded (2005) and Just My Luck (2006). In order to showcase her range, Lohan began choosing roles in independent films such as A Prairie Home Companion and Bobby (both 2006) and Chapter 27 (2007).

In 2013, under the guidance of Oprah Winfrey, Lohan filmed the docu-series Lindsay (2014), which depicted her returning to work. She subsequently made her stage debut in the London West End production of Speed-the-Plow (2014), starred in the second season of the comedy series Sick Note (2018), and served as a panelist in the first season of Masked Singer Australia (2019). Between 2016 and 2018, she opened three beach clubs in Greece, which were the focus of the MTV reality television series Lindsay Lohan's Beach Club (2019). After signing a multi-picture deal with Netflix, Lohan starred in the romantic comedy Falling for Christmas (2022).