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 Wallace Shawn Cyrus Rose Guest Star Margaret Colin Eleanor Waldorf Guest Star John Patrick Amedori Aaron Rose Guest Star Sam Robards Howie 'The Captain' Archibald Guest Star Connor Paolo Eric van der Woodsen Guest Star Robert John Burke Bart Bass Guest Star Josh Schwartz Executive Producer Stephanie Savage Executive Producer Jean de Segonzac Director Joshua Safran Writer