The answer is BOOTY The corresponding square is COMMUNITY CHEST 1 by Chris Morse Call of the Wild by Chris Morse Each of the sets of actors (who for the most part are cute) appear togeher in only one film. If you place the films into the grid below, the darkened boxes spell out "Solution word is BOOTY" (a quite appropriate answer). However, if you ALSO look at an acrostic of the movies, the letters spell out "Come to HQ and get a card" (which each team should come and do for an apparent reason) [***]. 1*Clueless - Paul Rudd + Jeremy Sisto 2*O - Josh Hartnett + Andrew Keegan 3*Mad Love - Chris O'Donnell + Matthew Lillard 4*Empire of the Sun - Christian Bale + Ben Stiller 5*To Wong Foo, Thanks for Everything, Julie Newmar - Jason London + Michael Vartan 6*Outside Providence - Jonathan Brandis + Adam Lavorgna 7*Head Over Heels - Freddie Prinze, Jr + Timothy Olyphant 8*Quiet Days in Hollywood - Chad Lowe + Jake Busey 9*A Few Good Men - Noah Wyle + James Marshall 10*Now and Then - Devon Sawa + Brendan Fraser 11*Dead in the Water - Henry Thomas + Scott Bairstow 12*Glory Daze - Matt Damon + Matthew McConaughey 13*Election - Chris Klein + Matthew Broderick 14*Twelve Monkeys - Jon Seda + Brad Pitt 15*Austin Powers in Goldmember - Seth Green + Josh Zuckerman 16*Crooked Hearts - Peter Berg + Joshua Jackson 17*Anything for Love - Corey Haim + Cameron Bancroft 18*Road Trip - Anthony Rapp + Seann William Scott 19*Dead Poet's Society - Josh Charles + Robert Sean Leonard [***] ed.: Except this was missed by almost all teams, in particular, the ones in the lead. When those teams had earned 8 hotels and tried to pick up the "deeds" leading to the coin, they were informed that they were in jail and, unfortunately, until they were out, we couldn't help them. They had to go back, examine their path around the board, and figure out that they must have picked up this card at this point. When they reviewed this puzzle long enough, they found what they had missed the first time.