Answer: Bruce Willis

It’s one thing to make a guest appearance outside your typical acting beat, but it’s another thing to make a guest appearance outside the genre fans expect to see you in and take home an Emmy for it.

In 2000, actor Bruce Willis, best known for his roles in films like Die Hard, The Sixth Sense, and The Fifth Element, appeared on Friends. Willis explained the appearance as the penance for a lost bet with Matthew Perry (Willis met the Friends star while they were filming The Whole Nine Yards).

The appearance ended up being a three episode story arc in the sixth season of Friends, where Willis played the role of Paul Stevens, the father of Ross’s girlfriend Elizabeth. The performance, with Paul naturally not taking to Ross and comedic interactions ensuing, was good enough to win Willis the Emmy for Outstanding Guest Actor In A Comedy Series.