uPick Win - Trampoline Wall-Walking

When do you go from “like a boss” to “actually a boss”? Because he may have done it.

(Source: cineraria)

How to Walk it Off Like a Boss [Click to animate]

She’s fine, she just dislocated her knee.

(Source: forgifs.com)

Tom Hanks Tapes Emmy to Hood of Car

I mean what are you gonna do with an Emmy, keep it on your fireplace?

(Source: twitter.com)

Larry Bird Makes Falling Look Cool

(Source: forgifs.com)

Old Man Casually Reads Playboy in Front of Family

Everyone has to wait till he’s done to start dinner.

(Source: College Humor)

The Cinnamon Challenge

(Source: College Humor)

{Click through for more}

(Source: College Humor)

(Source: College Humor)

(Source: College Humor)

Parallel Parking Like a Boss

Would you still be impressed if I told you he was parking in front of a Blockbuster to rent Dumb and Dumberer?

(Source: College Humor)

[Click to see more weird wedding videos.]

Good thing she knows how to rimshot since the institution of marriage is such a joke, am I right?

(Source: College Humor)

Jeopardy! Like a Boss

He pays Alex Trebek’s salary—in bossness.

Best Door to Door Salesman

Ladies and gentlemen, our generation’s Don Draper.