Bryan Cranston as Hammond Druthers
You likely know him from Breaking Bad and Malcolm In The Middle, but Bryan Cranston has had his fair share of guest-starring roles on sitcoms. One of the best though is definitely his role as Ted’s former boss Hammond Druthers. Not only is Druthers the worst boss in the world, but he also designs a building that looks more than a little bit like a certain male reproductive organ.
After working under Hammond, the roles reverse and Ted becomes the boss. Hammond still acts like a jerk though and Ted is forced to fire him. Unfortunately, Ted first tried to do this on Hammond’s birthday. He’s unable to go through with it though and waits until Druthers is going through a divorce.
Cranston reprised the role in season 9, after the conclusion of Breaking Bad and while it was a short, and rather insignificant appearance, the actor is still one of the show’s most legendary guest stars.