Lohan's early work won her childhood stardom, while the sleeper hit Mean Girls (2004) affirmed her status as a teen idol. After starring in Herbie: Fully Loaded (2005), Lohan quickly became the subject of intense media coverage due to a series of personal struggles and legal troubles, as well as a number of stints in rehabilitation facilities due to substance abuse. This period saw her lose several roles and had significantly impacted her career and public image negatively. Thereafter, she appeared in films, including A Prairie Home Companion (2006), Just My Luck (2006), Bobby (2006), and Chapter 27 (2007). In the 2010s, she appeared in few films, among the most notable being Machete (2010), Liz & Dick (2012), and The Canyons (2013). Lohan then appeared on a series of television shows including the docu-series Lindsay (2014), the British series Sick Note (2018), the MTV reality show Lindsay Lohan's Beach Club (2019), and The Masked Singer Australia (2019-present). She also made her stage debut in the London West End production of Speed-the-Plow (2014–15).
Lohan rose to prominence in the music industry under Casablanca Records, releasing two studio albums, the platinum-certified Speak (2004) and gold-certified A Little More Personal (Raw) (2005). Lohan dabbled in fashion, beginning a line of her own titled 6126 and briefly serving as artistic advisor for Emmanuel Ungaro in 2009. Since 2016, she has developed a series of nightclubs and resorts in Greece.