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 Michael Boatman Russell Thorpe Guest Star Francie Swift Anne Archibald Guest Star Connor Paolo Eric van der Woodsen Guest Star Clémence Poésy Eva Coupeau Guest Star Katie Cassidy Juliet Sharp Guest Star Tika Sumpter Raina Thorpe Guest Star Sam Robards Howie 'The Captain' Archibald Guest Star Michelle Trachtenberg Georgina Sparks Guest Star David Call Ben Donovan Guest Star Kaylee Defer Charlie Rhodes Guest Star William Baldwin Guest Star Josh Schwartz Executive Producer Stephanie Savage Executive Producer Leslie Morgenstein Executive Producer Bob Levy Executive Producer Joshua Safran Executive Producer, Writer Mark Piznarski Director Andrew McCarthy Director Sara Goodman Writer Leila Gerstein Writer Amanda Lasher Writer Patrick R. Norris Director J. Miller Tobin Director Joe Lazarov Director Tony Wharmby Director Janice Cooke Director Jeremiah S. Chechik Director Lee Shallat Chemel Director Ron Fortunato Director Tate Donovan Director