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 Francie Swift Anne Archibald Guest Star Sam Robards Howie 'The Captain' Archibald Guest Star Josh Schwartz Executive Producer Stephanie Savage Executive Producer Mark Piznarski Director K.J. Steinberg Writer Jessica Queller Writer