50 Best 'Mad Men' Characters

From one-off cameos to Sterling-Cooper's core players, we're ranking the show's most memorable characters

Guy MacKendrick

50. Guy MacKendrick

Showcase Episode: "Guy Walks Into an Advertising Agency"
Meet the new boss: Sterling Cooper gets a visit from Guy, the posh Brit who's running the shop from now on. He walks around shaking hands — polished, confident, every inch a gentleman. Except his first day at the office goes very, very badly, thanks to a runaway lawn mower. Poor Guy — introduced with so much fanfare, mopped up so fast. A perfect example of how Mad Men loves to set you up and then torpedo your expectations. As Joan says, "That's life. One day you're on top of the world, the next minute some secretary is running you over with a lawn mower."