In the winter of 2007/2008, Bastian team members Adam Frucci, Brandon Gardner and Brian Barrett formed the three person group "Classic Masculinity" after being asked to headline a show at the PIT hosted by the indie team MADAM. Brandon, who was coaching Madam at the time, got the name for "Classic Masculinity" from a line that Madam performer Peter Cook said in a rehearsal. Not actively seeking shows, Classic Masculinity did not perform again until that October when they were offered to be a substitute entry into the Cagematch season. In their second ever performance, Bastian defeated the 2007 Cagematch champions, C, C and C Improv Factory. After a week of unusually aggressive IRC trash talking, Classic Masculinity was defeated the following week by the 2006 Cagematch powerhouse Hot Sauce. This loss resulted in Classic Masculinity just barely missing the 2008 Cagematch Tournament by tying for 8th place with C, C and C Improv Factory, who made the tournament by virtue of having more total votes.