For me the most annoying transmissions are along the lines of: "Request any direct!" or "Any shortcut available today?", simply because one gets to hear those so often every day.
It's as if pilots believe ATCOs rejoice in not providing the shortest possible track the circumstances permit.
Also...quite irritating...seriously bad weather (e.g. heavy thunderstorms in the entire TMA, or runways not available due to heavy snowfall), and pilots asking..."Report reason for delay!"
One time one of my co-workers answered "Reason for delay is turtle race on the runway".
I know I know...not very professional, but all of us were struggling with massive traffic loads and dozens of aircraft in the holdings...