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chillin like a boss

The act of chilling, as a boss would do.
Ey look at TreShawn DeAndré, he be chillin like a boss.
by Autornoderator December 1, 2015
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Feelin' Like a Boss

Unlike when you do things like a boss, you apply it to your own self, your pride.

When you feel like a boss, you think you are the greatest thing in existence. You are so cool, that all the people around you want to be like you. People will sometimes say that you have swag.
"Damn, look at Nick!"

"Yeah, I see he's feelin' like a boss."

"I wanna be him some day."
by Ilisten2Metal June 5, 2014
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Like a boss

Used to describe something that someone did as amazing or awesome.
"Man, I just took that guy out like a boss!"

John faceplanted like a boss after getting hit with the dodgeball.
by flamingpeanut December 15, 2009
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Like A Boss

One of The Lonely Islands kick ass songs, which was pretty much a rip off Slim Thugs version.
Mr. Samberg Thanks for coming to your performance review
No problem
So you're in charge around here, is that fair to say?
Absolutely, I'm the boss
Okay, so take us through a day in the life of the boss
Well the first thing I do is...

Talk to to corporate (like a boss)
Approve memos (like a boss)
Lead a workshop (like a boss)
Remember birthdays (like a boss)
Direct workflow (like a boss)
My own bathroom (like a boss)
Micromanage (like a boss)
Promote Synergy (like a boss)
Hit on Debra (like a boss)
Get rejected (like a boss)
Sallow sadness (like a boss)
Send some faxes (like a boss)
Call a sex line (like a boss)
Cry deeply (like a boss)
Demand a refund (like a boss)
Eat a bagel (like a boss)
Harrassment lawsuit (like a boss)
No promotion (like a boss)
Fifth of vodka (like a boss)
Shit on Debra's desk (like a boss)
Buy a gun (like a boss)
In my mouth (like a boss)
Oh fuck man I can't fucking do it... shit!
Pussy out (like a boss)
Puke on Debra's desk (like a boss)
Jump out the window (like a boss)
Suck a dude's dick (like a boss)
Score some coke (like a boss)
Crash my car (like a boss)
Suck my own dick (like a boss)
Eat some chicken strips (like a boss)
Chop my balls off (like a boss)
Black out in the sewer (like a boss)
Meet a giant fish (like a boss)
Fuck its brains out (like a boss)
Turn into a jet (like a boss)
Bomb the Russians (like a boss)
Crash into the sun (like a boss)
Now I'm dead (like a boss)

Uh huh. So that's an average day for you then?
No doubt
You chop your balls off and die?
Hell yeah
And I think at one point there you said something about sucking your own dick
Nope!
Actually I'm pretty sure you did
Nah, that ain't me
Okay, well this has been eye opening for me
I'm the boss
Yeah, no I got that. You said it about four-hundred times
I'm the boss
Yeah yeah I got it!
I'm the boss
No I heard you, see ya later
LIKE A BOSS!
by Nemoxicated April 15, 2009
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Like A Boss

To do anything with authority even when its not needed or as a come back along the line of your face etc.
1: OMG man i just kicked his ass Like a Boss

2: you fucking suck!!!

like a boss
by MasterMind Grapes September 15, 2009
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like a boss

like you are in command or really mean somethin
man i fin ta wax that ass. "like a boss"
by Rod pimp c January 27, 2005
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Like A Boss

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.
by Girl Called Life July 14, 2011
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