The actress-and-singer - who is believed to currently be working on her third album - is keen to rework one of the pop star's biggest hits.
A source said: "Lindsay is on the Britney bandwagon. She is hoping to cover 'Womanizer' or 'Oops! ... I Did It Again'."
Lindsay became good friends with the 27-year-old singer in 2006, shortly after Britney filed for divorce from Kevin Federline.
The pair, along with socialite Paris Hilton, were regularly seen partying together in Los Angeles and Las Vegas, and were both photographed by the paparazzi not wearing any underwear.
Lindsay's latest record 'Spirit in the Dark' is reportedly packed with guest appearances, including Ne-Yo, Akon, Snoop Dogg, 50 Cent, Kanye West and Timbaland.
The 22-year-old star - who is dating DJ Samantha Ronson, the sister of super-producer Mark Ronson - recently claimed Pharrell Williams was also desperate to collaborate with her.
She said: "Pharrell is amazing. He said, 'I'd love to make a great record with you, but I want to take you out of all the elements that you're used to. Let's go somewhere nice where you can be focused.' "
Lindsay's pop career started with her recording songs for the films she starred in, including 'Herbie: Fully Loaded' and 'Confessions of a Teenage Drama Queen'.
She then released two albums 'Speak' in 2004 and 'A Little More Personal (Raw)' in 2005.
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