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outsider musician 

An outsider musican is a musician who is a social outcast or does not fit the norm. They are usually reclusive, anti-social, and sometimes cynically insane. They usually do not follow mainstream music rules and their lyrics are very emotional and sometimes strange. Some people enjoy and connect with the candidness of their lyrics while many people feel uncomfortable. Outsider musicians usually become well-known through word of mouth.
Some examples of popular outsider musicians are: Daniel Johnston, Syd Barrett, Larry "Wild Man" Fischer, and The Shaggs. (just to name a few)

outsider trading 

Buying, selling, and trading in the stock market without knowing what the fuck you are doing AT ALL.
I got involved in some outsider trading and lost 40 million dollars in one day.

Outsider's Edge 

Jerking off with your hand on the outside of your pants, i.e. in class, at work, or while driving.
Harris was giving himself the Outsider's Edge during government class yesterday...he thought no one knew, but we all saw the stain.
Outsider's Edge by BHunt September 21, 2003

The Cuban Outsider 

wow that was a deep shot by the Cuban Outsider
The Cuban Outsider by Kody Wade November 19, 2009

Wannabe Outsider 

A wannabe outsider is the type of person who would do anything to be original, but, in reality once you figure out what he/she is doing its pretty pathetic. Here are some quirks of a wannabe outsider

1) He/she almost always go to reseraunts that no one goes to

2) Think and talk about emotional representations of things when you have known him/her for years and they have never talked like that before

3) When confronted about being a wannabe of anykind, he/she will call you out on personal things(like you don't have a girlfriend, etc)
Wannabe outsider: Hey lets go to this resteraunt that no one has ever heard of, they sell the best burgers and fries!

Normal person(you): How about burger king(or any other mainstream resteraunts)

Wannabe outsider: Nah I have never liked fast food

Normal person(you): But you just said an underground food place that sells fast foo.... you are such a wannabe outsider

Rank Outsider

A particularly bad fart committed in an enclosed space: It's rank and you wish it was outside.
Bloody Nora, luv. What have you eaten? That one's a rank outsider. (HM Elizabeth II to Prince Phillip on tour in Thailand 2006)