Age: 25 Best Known For: Chuck Bass in Gossip Girl Why Hed Be Good: Hes got the arrogant, unnerving charm thing going on. As Chuck Bass he plays an alienated, friendless spoiled rich bastard. Season Four of Gossip Girl contained a bit of controversy when Chuck becomes violent with girlfriend Blair Waldorf, adding even more fire to their volatile relationship. Why He Wouldn't: Theres got to be something soft and vulnerable behind the Gucci suit exterior. Is Ed just a little too cold?