How many movies have Bob Sheppard and John C. Reilly acted in together?

They have worked on 2 movies together! Their first movie together was For Love of the Game (1999) and was their highest rated movie together. They have not worked together since Anger Management (2003).

Anger Management (2003)

Role
The Voice of the Yankees
Role
Older Arnie Shankman (uncredited)

For Love of the Game (1999)

Role
Yankee Stadium Announcer (as Robert Leo Sheppard)
Role
Gus Sinski