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5 o'clock cheesy shadow 

When one develops an orange stain around the lower face after a day of sitting on the couch and eating Cheetos.

The mark of a true couch potato.
Girl 1: I come home from work every day and my orange-faced boyfriend is just sitting there with the remote.

Girl 2: Uh oh, its a 5 o'clock cheesy shadow.

5 o'clock Charlie 

When your boss does somethnig just as you're about to clock out that fucks up the rest of your day or weekend. Typically, this is comprised of a request for you to do some work and is due to laziness and/or lack of preparedness on their part.

This is a reference to an episode of MASH where the enemy would fly in everyday at 5 o'cock and drop a bomb on the camp's garbage pile.
Darcy is such a shitty boss. She came in to my office just as I was clocking out and told me she needed the last 2 weeks of bank records before I go. She knew about this request a long time ago but since she sucks as a manager and a human being, she thinks it's okay to routinely drop these 5 o'clock Charlies in my lap.

5 o'clock free crack give a way 

Definition 1: A Free Crack Giveaway at 5 o'clock.

Definition 2: A really good deal

Definition 3: An Out-of-Control Party
ex. 1: A five o'clock free crack give away, wow , that's a low price!

ex. 2: A free car? That's a five o'clock free crack give away

ex. 3: Jesus, this partie's like a 5 o'clock free crack give a way.

5 o'clock slop 

The dirtiest of the dirty, the most unattractive girl at the bar and your last option if you want to get laid that night. This girl is usually so unattractive 2am isn't enough time to drink to make her worth it, around 5 is when she becomes an option
Man i must have of been hammered last night i woke up next to a real piece of 5 o'clock slop.

see also road whore
5 o'clock slop by king dingaling89 October 26, 2010

5 o'clock block 

the prompt 4:54pm Friday evening arrival of a certain visitor with a critical (due today) case that has been sitting on that visitor’s desk for 5 months and 29 days – yet needs to be out today!
F: Damn, I can't make the party tonight! I just got 5 o'clock blocked by one of my bosses! I'll be pulling another all-nighter tonight!

G: 5 o'clock-blocked again!? That excuse is getting old.
5 o'clock block by 5 o'clock-blockee September 16, 2011

5 o'clock flush 

When the majority of aircraft finish the flying for the day around the same time...generally around 1700L, and the crews write up maintanence issues. As result, many trips for the following day are put back in the uncovered file resulting in a 5 o'clock flush.
Boss, "Why do we have 12 trips for tomorrow still uncovered?"

Scheduler, " We just had 7 aircraft all finish their day and the crews wrote up their aircraft."

Boss, "Ahh, the 5 o'clock flush".