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Williams has credited Dawson's Creek as "the best acting class", but also admitted that she had not fully invested herself in it as "my taste was in contradiction to what I was doing every single day".
Penned by Tracy Letts, it is a black comedy about a dysfunctional family who kills their matriarch for insurance money; Williams was cast as the family's youngest daughter.
In 1998, Williams began starring in the television teen drama series Dawson's Creek, created by Kevin Williamson and co-starring James Van Der Beek, Katie Holmes, and Joshua Jackson.
The series aired for six seasons from January 1998 to May 2003 and featured Williams as Jen Lindley, a precocious and promiscuous New York-based teenager who relocates to the fictional town of Capeside.
The series was filmed in the small town of Wilmington, North Carolina, where Williams relocated for the next six years.
In a review of the first season for The New York Times, Caryn James called it a soap opera that was "redeemed by intelligence and sharp writing" but thought that Williams was "too earnest to suit this otherwise shrewdly tongue-in-cheek cast".
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Her next role was in the HBO television film If These Walls Could Talk 2 (2000), a drama about three lesbian couples in different time periods.
She began her career at a young age with television guest appearances and made her feature film debut in the family film Lassie (1994).