How I Met Your Mother: 10 Best Supporting Characters
8. Hammond Druthers
Hammond Druthers was played expertly by Bryan Cranston, who may be best known for playing Walter White on Breaking Bad, but he's just as at home in comedy, which is clear seeing him take on the role of Ted's insanely vindictive and uncompromising boss at his architecture firm.
Druthers is an unapologetic a**hole, who Ted barely tolerates. He appeared in three episodes, and in each one, he's not someone you'd like to meet without a Taser in your hands. In his first appearance, he falls prey to some "Aldrin Justice" when Lily takes his ball signed three times by Pete Rose after she sees how badly he behaves.
His building design was revealed to resemble male genitalia, so when Ted speaks up, his design is bought by the clients, giving him his boss' job, and putting Druthers under his supervision. Of course, Druthers becomes a nightmare, and Ted has to fire him, which doesn't go well.
He ends up latching onto Ted in the hopes of keeping his job, but eventually pushes him too far, so Ted fires him as he's having a heart attack. He appeared in the final season once more to try and pull Ted to Chicago to work for his firm, but Ted refuses, so Druthers threatens Ted, but to no avail.