Blake Lively Serena van der Woodsen Actor Leighton Meester Blair Waldorf Actor Penn Badgley Dan Humphrey Actor Chace Crawford Nate Archibald Actor Taylor Momsen Jenny Humphrey Actor Ed Westwick Chuck Bass Actor Jessica Szohr Vanessa Abrams Actor Kelly Rutherford Lily van der Woodsen Actor Matthew Settle Rufus Humphrey Actor Hilary Duff Olivia Burke Guest Star Tyra Banks Ursula Nyquist Guest Star Tory Burch Self Georgina Chapman Self Josh Schwartz Executive Producer Stephanie Savage Executive Producer Bob Levy Executive Producer Leslie Morgenstein Executive Producer John Stephens Executive Producer, Writer Mark Piznarski Director