8
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 13, 2011
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9
1. to really excell at something. to succeed with extreme luck or ease.
2. to run a program with administrator privileges in later versions of windows.
1. terrence played call of duty like a boss when he no scope headshot the opposing team's last guy from a mile away

2.Roy: I can't get this new game to to run on windows 7.
tommy: have you tried running it like a boss?
by masteroffire December 09, 2011
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10
1. - Doing something or "holdin' it down" better than anybody or anything else in the history of everything ever.
2. - That awesome moment when you handyman-the-fuck out of a sticky household catastrophe successfully (and by yo'damn self) and then proceed to do that thing where you walk past a mirror, pointing at yourself from the side without-even-looking, knowing beyond a shadow of a doubt that, for at least one brief moment, YOU are the King Dingaling of the Universe.
"Fixed the bathroom sink like a boss."
by B-Diddle August 22, 2013
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11
During a critical moment, a person, animal or thing seizes the oppurtunity and takes charge and wins or overcomes an obstacle that seems nearly impossible to accomplish. A website has also been created due to this saying: LikeABoss(dot)com
Conner Long is nine years old. His little brother Cayden is seven. But Cayden can’t do a lot of things his big brother can do. At four months old, Cayden was diagnosed with a condition called hypertonic cerebral palsy, which leaves him unable to walk or talk on his own. Playing sports is a great way for brothers to bond, but it seemed to be out of the question for the Longs — until Conner had an idea.

A year and a half ago, he and Cayden started participating in triathlons together. Conner swims while pulling Cayden in a raft, bikes with his little brother towed behind him in a trailer, and pushes that trailer when they run. Over the past 18 months, the pair from White House, Tennessee, traveled up and down the East coast to compete in races. Seeing the brothers working together has inspired onlookers, while bringing Conner and Cayden closer than ever. Their amazing determination and spirit is why the Long brothers are the 2012 Sports Illustrated Kids SportsKids of the Year.

Conner Long is Like A Boss.
by LockyOnline August 07, 2013
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12
when your the booosssssss :)

you suck your own dick, chop your balls off and die: this is an average day!
shit on debras desk - like a boss
by imtheboss June 02, 2009
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13
Your ontop on the World your the Boss you've stepped your game up and now you libe a Boss lifestyle.
Talk to corporate LikeaBoss!
by elal January 07, 2011
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14
A phrase everything thinks was started by Andy Samberg and The Lonely Island from their song "Like A Boss"

Mistakenly "Like a Boss" originated from Slim Thug, who is still a boss.
Guy 1: "Yo I plowed this chick last night in the back of my Benz"

Guy 2: "Like a boss?"

Guy 3: "No like a normal kid who's Dad is a lawyer"
by cranvicted December 16, 2009
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