The Office: 10 Best Characters Only In One Episode

Episode: Season 2, Episode 11 - "Booze Cruise"

Portrayed By: Rob Riggle

When Michael took the team out on a Booze Cruise, he did so aboard a vessel captained by one Captain Jack, as played by Rob Riggle. Almost immediately, the two men have problems with one another, with the Captain being the one who had more issues with Michael rather than the other way around.

Captain Jack was in the United States Navy during the Gulf War, and he had a few close calls. There isn't much more known about his backstory other than the fact that he proposed to his first wife the day he returned from the war, though, they later divorced.

Michael and Jack didn't get along throughout the Booze Cruise, mostly due to Michael's challenging of Jack's authority. When Jack was getting it on with Meredith, their rendezvous was interrupted when he heard Michael outside trying to convince the passengers the boat was sinking, and that Jack abandoned them to their fate.

After Jack came out to find everyone in a panic, he put Michael in the brig, which is to say, he zip-stripped him and sent him to the back of the ship, but it was after a passenger jumped through a window into the water.