Adam McKay makes it clear in this THR article that Will Ferrell apparently had no problem casting Michael Shannon as Jerry Bass for Win Time. It seems McKay was also very happy to have on board the respected actor Shannon, who played the most pivotal role in the series. Unfortunately, as production got closer, Shannon grew weary of the concert, and eventually left the series under the time-honoured Hollywood slogan of “creative differences”.
While Shannon has been generally quiet about his late departure from Winning Time, McKay shed a little more light on the matter in THR. And according to McKay, Shannon never agreed with any of the central elements of the show’s frame, most notably the breaking of the fourth wall. This method, in which a character speaks directly to the audience in a scene to give additional information, has become an integral part of McKay’s aesthetic over the years, so it’s not surprising that he would also be prominent in Win Time.
However, as McKay noted to THR, “Michael was really concerned that we were breaking the fourth wall.” The ‘Victory Time’ creator added: ‘He kept saying, ‘I don’t like this. It baffles me. It’s hard for me.” In the end, Shannon decided that he was just uncomfortable moving forward with these fourths … the wall breaks on the spot. And if you’ve seen Win Time, you know they’re very important to Jerry Bass’ storytelling, so McKay really couldn’t just skip them. In the end, John C. Reilly ran with them and delivered one of his best performances to date, leaving you wondering why he wasn’t offered the part from the start.