Shane Gillis Shane Creator, Actor, Executive Producer, Writer Steve Gerben Will Creator, Actor, Executive Producer, Writer John McKeever Creator, Executive Producer, Writer, Director Chris O'Connor Cal Actor Kilah Fox Kilah Actor Stavros Halkias Dave Actor Andrew Schulz Schulz Actor Chip Chantry Kyle Guest Star Victoria Harrington Desiree Guest Star Brooke Edelstein Barb Guest Star Peter Reeves Jonathan Guest Star Tommy Pope Tommy Actor Rachel Keefe Amber Guest Star Bob Senkewicz Arnold Guest Star Charles Blyzniuk Reporter Actor Luke Kenney Cooch Guest Star Emely Cartagena Alexis Guest Star Becca Jackson Jaeymee Guest Star Brandon James Executive Producer Brian Stern Executive Producer Becky Astphan Executive Producer Kenneth Slotnick Executive Producer