Hudson's breakthrough role was as Penny Lane in Cameron Crowe's Almost Famous (2000), for which she received an Academy Award nomination for Best Supporting Actress and won the Golden Globe Award for Best Supporting Actress. She had previously appeared in the lesser-known films Gossip, a teenage drama, and 200 Cigarettes, a New Year's-set comedy with a large cast of actors. Regarding her early career and success, Hudson has noted that she is a "hard worker", and did not want to be associated with her well-known parents, wishing to avoid the perception that she "rode on somebody's coattails".

In the 2002 Hudson starred in remake of the historical romance The Four Feathers, a film which was not well received by critics or audiences. Her next film, How to Lose a Guy in 10 Days, a romantic comedy, became a big success at the box office, grossing over $100 million after its February 2003 release. Hudson subsequently appeared in several romantic comedies, including Alex and Emma and