This was a common Marine Corps Drill Instructor phrase that could be used in a sarcaatic context and but also has meaning within the context of a bonafide compliment.

In sarcastic context it is used to immediately reinforce the message that someone had just screwed up so royally that
it would permanently alter people's perceptions about that someone from that moment onward.

In the positive context it means that your applaud and commend the actions of another with the goal of motivating them to high levels of performance.
Sarcastic usage: Young man has to go to her father and explain that she is pregnant and you are the father. His first words: "Out-fucking-standing! Want to go hunting with Dick Cheney?" In this context the delivery is slow with deliberate accent heavily on the "out," the "fuck," and the "stand." There is also a slight pause between each syllable.

In the positive context no heavy accenting nor does one pause between syllables but the comment is meant in a way that encourages and motivates to new levels of performance.
Context: Your girlfriend shows up in a coat, opens it to display nothing underneath, and stares you in the eye with desire. Your reply is a happy: "Out-fucking-standing@"

by WinningAttitude March 17, 2007
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From military lexicon that combines the words "outstanding" and "fuck" together to mean just the opposite of the word "outstanding" Usually describes a person(s) or situation(s) that are totally and completely fucked up beyond all recgonition. Also used in texting shorthand.
Trooper 1: "Lt. BooBoo just got his whole squad captured during the exercise, but he escaped". Trooper 2: "(OTFS) Out the fuck standing"! Trooper 1: "What a joke, let's go smoke a bowl". Trooper 2: "Cool".
by sliptrip August 19, 2011
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