Blake Lively Serena van der Woodsen Actor Leighton Meester Blair Waldorf Actor Chace Crawford Nate Archibald Actor Penn Badgley Dan Humphrey Actor Taylor Momsen Jenny Humphrey Actor Ed Westwick Chuck Bass Actor Kelly Rutherford Lily van der Woodsen Actor Matthew Settle Rufus Humphrey Actor Connor Paolo Guest Star Jay McInerney Guest Star Tinsley Mortimer Guest Star Mädchen Amick Guest Star Patrick Heusinger Guest Star Alex Carl Laurel's Assistant Guest Star Josh Schwartz Executive Producer Stephanie Savage Executive Producer J. Miller Tobin Director Joshua Safran Writer