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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
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
What you say to make things soud cooler/more exiting then it actually is.

originated from the song like a boss, by the lonley island.
yeah, i did my homework. like a boss
by paperchasesme May 09, 2009
Somebody who does something others would be too afraid because the boss follows his own free will. Someone who does whatever he/she wants, not because morons think it's cool.
Will - "Dude, Matt went skydiving."

Robbie - "LIKE A BOSS!"

Will - "Dude, Matt killed Justin Beiber."

Robbie - "LIKE A BOSS!"

Will - "Dude, Matt sucked a -"

Robbie - "LIKE A BOSS!"
by Stephan J. August 18, 2014
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
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
Performed with excellence and authority. This usually refers to dealing with difficult or unusual situations, implying assertiveness and excellence. This term has been used in the Caribbean and in particular Trinidad since at least the 1980s.
To compliment a friend talking his/her way out of a speeding ticket... "Boy, you handled that cop like a boss!"
by primediggydee April 11, 2013