James Van Der Beek, Jessica Biel, Kate Bosworth, Kip Pardue, Ian Somerhalder, and Shannyn Sossamon in The Rules of Attraction (2002)

James Van Der Beek, Katie Holmes, Joshua Jackson, Kerr Smith, and Michelle Williams in Dawson's Creek (1998)

James Van Der Beek, Katie Holmes, Joshua Jackson, and Michelle Williams in Dawson's Creek (1998)

James Van Der Beek, Scott Caan, Ali Larter, Amy Smart, and Paul Walker in Varsity Blues (1999)

James Van Der Beek, Katie Holmes, Joshua Jackson, Meredith Monroe, and Michelle Williams in Dawson's Creek (1998)

James Van Der Beek, Katie Holmes, and Michelle Williams in Dawson's Creek (1998)

James Van Der Beek, Scott Caan, Ali Larter, Amy Smart, Ron Lester, Eliel Swinton, and Paul Walker in Varsity Blues (1999)

James Van Der Beek, Jessica Biel, Ian Somerhalder, and Shannyn Sossamon in The Rules of Attraction (2002)

James Van Der Beek, Ali Larter, Amy Smart, Ron Lester, Eliel Swinton, and Paul Walker in Varsity Blues (1999)

James Van Der Beek in What Would Diplo Do? (2017)

James Van Der Beek, Dora Madison, Michael Croner, and Dillon Francis in What Would Diplo Do? (2017)

James Van Der Beek and Krysten Ritter in Don't Trust the B---- in Apartment 23 (2012)

James Van Der Beek in Aliens in the Family (1996)

James Van Der Beek in Saturday Night Live (1975)

James Van Der Beek in Under a Rock with Tig Notaro (2019)

James Van Der Beek, Anthony Anderson, Kate Flannery, and Jack McBrayer in Match Game (2016)

Alec Baldwin, James Van Der Beek, Anthony Anderson, Kate Flannery, Jenifer Lewis, Jack McBrayer, and Ellie Kemper in Match Game (2016)

James Van Der Beek and Jenifer Lewis in Match Game (2016)

James Van Der Beek, Anthony Anderson, Kate Flannery, Jenifer Lewis, Jack McBrayer, and Ellie Kemper in Match Game (2016)

James Van Der Beek, Anthony Anderson, Yvette Nicole Brown, Jack McBrayer, Anna Camp, and Ellie Kemper in Match Game (2016)

Matt Damon, James Van Der Beek, Kristen Wiig, and Alison J. Palmer in Downsizing (2017)

James Van Der Beek, Josh Lucas, and Holt McCallany in Stolen (2009)

James Van Der Beek, James Corden, Jim Gaffigan, and Liam Payne in The Late Late Show with James Corden (2015)

James Van Der Beek and Taylor Schilling in Mercy (2009)

James Van Der Beek, Katie Holmes, Joshua Jackson, Meredith Monroe, Kerr Smith, and Michelle Williams in Dawson's Creek (1998)

James Van Der Beek, Katie Holmes, Joshua Jackson, Busy Philipps, Kerr Smith, and Michelle Williams in Dawson's Creek (1998)

James Van Der Beek and Ivana Milicevic in The Plague (2006)