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The day in your organization that you can separate the biggest brown nose from the rest of the employee's. This person will almost automatically show up with a gift from themselves for the boss before anyone else, thus grasping that little bit o' shit that will complete the engulfment of the nose of the presiding ass kisser. This is usually a closely related ailment of a combination sexual/social disorder that prohibits the person from actively seeking a random ass to kiss while struggling with being stuck in the body of the wrong sexual gender.
Here he comes with a box of new knee pads for you-know-who...must be Boss' Day
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The Stranger with an assist. Have another person hit you in the cluster of nerves in your armpit with their thumb, causing your arm to go completely numb. Then, with your working arm, grab your dead arm and jerk yourself off.
After a long day, my buddy treated me to a pit boss.
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If one is cole bossing, one is achieving the maximum level of dominance in the world, portraying their true inner personality in the most positive way possible. If one is told that they are cole bossing, they have achieved the maximum level of recognition that one can receive. It is essentially girl bossing, but monumentally better. It can of course be used more casually to just say that one is an awesome person, but overall cole boss is the highest of compliments.
Yo I saw you score 25 points in the basketball game; keep on cole bossing.
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The ultimate in pimpery, debauchery, and anything baller/good.
"Wow, that dude bagged the hottest girl, he's a Boss-Tycoon. HOLLA"
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When you are horny and on your period, thereby preventing you from having sex.
Guy: You slapping the boss right now?
Girl: Yes! I am so horny but I'm on my period...
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Based on the song "Like A Boss" by Andy Samberg and Lonely Island Boys.
The lyrics are about the responsibility of power or lack thereof. The concept behind the song is loosely based on individuals in contemporary pop culture (i.e. rap stars) who insist they're the most amazing person in the universe but are, in reality, rather ridiculous.
This scenario directly effects the meaning of the phrase. While most would say it signifies an increased level of "awesomeness" in a given situation, the context the phrase was originally used in would suggest the opposite.
The point of it is that you're saying you're awesome using a terminology that's based on making fun of people who say they're awesome. The irony makes it hilarious, especially because the term has run rampant and most people who say it don't realize that they're, in essence, making fun of themselves unknowingly. Double funny.
It can also be used in a sarcastic, summarizing capacity (see example below).
With the irony of it in mind, you can interchange it with longer explanations as I did in a Facebook post once:
By saying, "like a boss" what I'm really saying is, "my very busy and overextended work schedule is contributing to a substantial increase in the amount of alcohol I consume and it's not only pathetic, but also not exemplary of the type of behavior that's indicative of upper management."
Just realized it's 6:12 PM and I was SO busy today that I didn't eat, I still haven't checked my voice mail and I've had to pee for the last 4 hours. Who needs a glass of wine? This girl right here. Like a boss.
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