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 Amara Zaragoza Poppy Lifton Guest Star Armie Hammer Gabriel Edwards Guest Star James Naughton William van der Bilt Guest Star Jessica Szohr Vanessa Abrams Actor Josh Schwartz Executive Producer Stephanie Savage Executive Producer John Stephens Director Amanda Lasher Writer