How many movies have Holmes Osborne and Vince Vaughn acted in together?

They have worked on 3 movies together! Their first movie together was Domestic Disturbance (2001) while their highest rated movie together was Anchorman: The Legend of Ron Burgundy (2004). They have not worked together since Wake Up, Ron Burgundy: The Lost Movie (2004). They are most known for their comedy films together.