During The Office's third season, Krasinski got his first big film offer alongside George Clooney in the 2008 film Leatherheads. There was only one thing standing in his way.
Office makeup artist Kim Ferry remembers, "It would have meant cutting his hair into a 1920s hairstyle. But continuity-wise and contractually-wise, actors are obligated to keep their hair how it is for a series unless they get producer approval, of course. [...] He came to me and said, 'Could we do a wig?' He went to talk to them and said, 'I really want to do this project.' And they were like, 'I think it would be obvious that it was a wig.' Greg [Daniels, the showrunner] really felt it won't look like him."
According to Ferry, Krasinski came up with a solution. "Hiring a wig maker is not inexpensive," she says. "We did the fitting in his trailer and when it was done it looked amazing. It looked exactly like him." They still, however, had to convince Daniels.
Ferry said that she tracked down Krasinski and found him in Daniels' office, recalling that she saw the wig, "sitting on Greg's desk. John told me later that Greg said to him, 'John, I'll know if it's a wig. You can't fake that kind of thing.' As he's staring at him with the wig on. And then John's like, 'Really? I don't think you would,' and he takes it off right in front of him. And then Greg said, 'You win, I give you full permission to wear the wig.' When I came in, [Greg] said to me, 'You guys have a lot of b***s.' For a minute I really thought I was going to get fired."